o-nitrostyrene reference compilation

[GC_MS]

What follows is a compilation of omega-nitrostyrene syntheses taken from Houben-Weyl. There are 5 threads (forum does not accept post with more than 10000 chars, so I split the references up in the most convenient way):

- benzaldehydes with nitromethane (pt 1 + 2)
- benzaldehydes with nitroethane
- benzaldehydes with nitropropane
- benzaldehydes with nitrobutane

Reference: Houben-Weyl, Methoden der organischen Chemie. Band X/1, Stickstoffverbindungen I, Teil I, pp 342-357

The "PARTS" agree with different pages from H-W. Hence, many references are mentioned several times.

Used abreviations for references:

A                    Liebigs Annalen der Chemie
Am Soc               Journal of the American Chemical Society
Ang Ch               Angewandte Chemie
Ar                   Archiv der Pharmazie
B                    Berichte der Deutschen Chemischen Gesellschaft
Bl                   Bulletin de la Societe Chimique de France
C                    Chemisches Zentralblatt
CA                   Chemical Abstracts
Canad J Res          Canadian Journal of Research
CR                   Comptes Rondus Hebdomadaires des Seances de l'Academie des Sciences
Doklady Akad SSSR    Doklady Akademii Nauk SSSR (Russian) (aka CR de l'Academie des
                     Sciences de l'Union des Republiques Sovietiques Socialistes)
Helv                 Helvetica Chimica Acta
J agr chem Soc Japan Journal of the agricultural and chemical Society of Japan
J Indian chem Soc    Journal of the Indian Chemical Society
J Org Chem           Journal of Organic Chemistry
J Pharm Soc Japan    Journal of the Pharmaceutical Society of Japan
J pr                 Journal fuer Praktische Chemie
M                    Monatshefte fuer Chemie
Org Synth Coll       Organic Synthesis Collection
R                    Recueil des Travaux Chimiques des Pays-Bas
S P In phys chem Res Scientific Papers of the Institute of Physical and Chemical Research. Tokyo
Soc                  Journal of the Chemical Society. London
Z obsc Chim          Zurnal Obscej Chimii (Russian) (aka Journal of General Chemistry)
Z Org Chim           Journal of Organic Chemistry (Russian)

[GC_MS]

Format: precursor, yield, reference(s)

PART 1

benzaldehyde, 80-83, [1-7]
4-methylbenzaldehyde, *, [7,8]
2-fluorbenzaldehyde, 70-75, [9,10]
2-chlorobenzaldehyde, *, [7,11,12]
3-chlorobenzaldehyde, 34, [7,12]
4-chlorobenzaldehyde, *, [7,12,13]
2-bromobenzaldehyde, 50, [12-14]
3-bromobenzaldehyde, *, [15]
4-bromobenzaldehyde, *, [11]
2-iodobenzaldehyde, 65-70, [16]
2-nitrobenzaldehyde, *, [7,13,17,18]
3-nitrobenzaldehyde, 76, [3,7,11,13,19,20]
4-nitrobenzaldehyde, *, [3,5,7,13]
3-cyanobenzaldehyde, 42, [21]
3-thiocyanatbenzaldehyde, 80, [22]
4-thiocyanatbenzaldehyde, 70, [22]
2-carboxybenzaldehyde, *, [7,23]

[1] B Priebs, A 225, 319 (1884); DE Worrall, Org Synth Coll Vol I, 405 (1932)
[2] E Knoevenagel, L Walter, B 37, 4502 (1904)
[3] J Thiele, B 32, 1293 (1899)
[4] M Holleman, R 23, 283 (1904)
[5] J Thiele, S Haeckel, A 325, 1 (1902)
[6] CB Gairaud, GR Lappin, J Org Chem 18, 1 (1953)
[7] M Koremura, H Oku, T Shono, T Nakanishi, Takamine Kenkyusho Nempo 13, 205 (1961) [CA 57.16450 (1962)]
[8] DE Worral, Am Soc 60, 2841 (1938)
[9] AV Topchiev, VP Alaniya, MF Vagin, Doklady Akad SSSR 151, 114 (1963) [CA 59.10245 (1963)]
[10] DE Worral, HT Wolosinki, Am Soc 62, 2449 (1940)
[11] DE Worral, Am Soc 56, 1556 (1934)
[12] N Campbell, W Anderson, J Gilmore, Soc (1940) 446
[13] FGP Remfry, Soc 99, 282 (1911)
[14] DE Worrall, J Finkel, Am Soc 61, 2969 (1939)
[15] H Kondo, S Ishiwata, B 64, 1533 (1931)
[16] DE Worrall, F Benington, Am Soc 62, 493 (1940)
[17] L Bouveault, A Wahl, C R 135, 41 (1902); C (1902) II, 449
[18] L Bouveault, A Wahl, Bl [3] 29, 521 (1903)
[19] K H Slotta, G Szyszka, B 68, 184 (1935)
[20] AK De, J Indian Chem Soc 5, 29 (1928); C (1928) I, 2393
[21] KH Slotta, R Kethur, B 71, 59 (1938)
[22] JP19155 (1964) [CA 62.7864 (1965)]
[23] T Hashimoto, S Nagase, J Pharm Soc Japan 80, 1637 (1960) [CA 55.7415 (1961)]

---

PART 2

2-hydroxybenzaldehyde, 34, [1-3]
3-hydroxybenzaldehyde, 66, [2,3]
4-hydroxybenzaldehyde, 60, [1,2,4]
4-acetoxybenzaldehyde, 11, [2,3]
4-benzyloxybenzaldehyde, *, [5]
3-benzyloxybenzaldehyde, *, [6]
4-benzoylbenzaldehyde, *, [2,5]
2-methoxybenzaldehyde, 82, [4]
3-methoxybenzaldehyde, *, [7]
4-methoxybenzaldehyde, 86, [1,4,8-15]
2-ethoxybenzaldehyde, 30, [4,16]
4-dimethylaminobenzaldehyde, *, [1,17]
4-diethylaminobenzaldehyde, 70, [16]
4-acetaminobenzaldehyde, 89, [1,16]
4-methylmercaptobenzaldehyde, *, [18]
4-ethylmercaptobenzaldehyde, *, [18]
4-allylmercaptobenzaldehyde, *, [18]
4-propyn-1-ylmercaptobenzaldehyde, *, [18]
4-aminosulfonbenzaldehyde, *, [19]
2,4-dichlorobenzaldehyde, 62, [1,20]
2,6-dichlorobenzaldehyde, 74, [16]
3,4-dichlorobenzaldehyde, *, [1]

[1] M Koremura, H Oku, T Shono, T Nakanishi, Takamine Kenkyusho Nempo 13, 205 (1961) [CA 57.16450 (1962)]
[2] FGP Remfry, Soc 99, 282 (1911)
[3] G Hahn, K Stiehl, B 71, 2154 (1938)
[4] CB Gairaud, GR Lappin, J Org Chem 18, 1 (1953)
[5] KW Rosenmund, B 46, 1034 (1913)
[6] H Kondo, S Ishiwata, B 64, 1533 (1931)
[7] JB Shoesmith, RJ Connor, Soc (1927) 2230
[8] DE Worrall, Am Soc 56, 1556 (1934)
[9] L Bouveault, A Wahl, C R 135, 41 (1902); C (1902) II, 449
[10] E Knoevenagel, L Walter, B 37, 4502 (1904)
[11] L Bouveault, A Wahl, Bl [3] 29, 521 (1903)
[12] KW Rosenmund, B 42, 4778 (1909)
[13] T Kondo, Y Shinozaki, J Pharm Soc Japan 49, 267 (1929) [CA 24.5294 (1930)]
[14] MPJM Jansen, R 50, 291 (1931)
[15] DE161171
[16] O Schales, HA Graefe, Am Soc 74, 4486 (1952)
[17] JR Merchant, SR Agrawal, J Indian chem Soc 40, 472 (1963) [CA 59.9846 (1963)]
[18] JP28323 [CA 62.11739 (1965)]
[19] JP467 [CA 59.11380 (1963)]
[20] MB Neher, EW Goldberg, RW Fairchild, J Org Chem 26, 5220 (1961)

---

PART 3

2,3,6-trichlorobenzaldehyde, *, [1]
4-chloro-3-nitrobenzaldehyde, *, [2]
2-chloro-3-ethoxybenzaldehyde, 76, [3]
3-bromo-4-methoxybenzaldehyde, *, [4]
4-methoxy-3-chloromethylbenzaldehyde, *, [5]
3,5-dichloro-4-hydroxybenzaldehyde, 50, [6]
2,6-dichloro-3-methoxybenzaldehyde, 70, [7]
4-chloro-3-hydroxybenzaldehyde, 60, [2]
2-chloro-3-hydroxybenzaldehyde, 70, [7]
2-chloro-3-methoxybenzaldehyde, 80, [7]
4-chloro-3-rhodanbenzaldehyde, 50, [2]
5-chloro-2-hydroxybenzaldehyde, 12, [8]
3,4-dihydroxybenzaldehyde, *, [5]
2-hydroxy-4-methoxybenzaldehyde, *, [9]
2-hydroxy-3-methoxybenzaldehyde, 78, [10,11]
3-hydroxy-4-methoxybenzaldehyde, 63, [12,13]

[1] US3112346
[2] JP 28318 [CA 62.11736 (1965)]
[3] GS Sidhu, PB Sattur, SJ Hasan. J Sci Ind Research (India) 19C, 38 (1960) [CA 55.15381 (1961)]
[4] M Kondo, S Ishiwata, B 64, 1533 (1931)
[5] M Koremura, H Oku, T Shono, T Nakanishi, Takamine Kenkyusho Nempo 13, 205 (1961) [CA 57.16450 (1962)]
[6] JP26960 [CA 62.14569 (1965)]
[7] GS Sidhu, PB Sattur, SJ Hasan. J Sci Ind Research (India) 19C, 38 (1960) [CA 55.15381 (1961)] (sic)
[8] O Schales, HA Graeffe, Am Soc 74, 4486 (1952)
[9] MGS Rao, C Srikantia, MS Iyengar, Helv 12, 581 (1929)
[10] CB Gairaud, GR Lappin, J Org Chem 18, 1 (1953)
[11] VG Voronin, GD Kulikovskaya, LD Magda, Z Org Chim 1, 719 (1965) [CA 63.5546 (1965)]
[12] G Hahn, K Stiehl, B 71, 2154 (1938)
[13] G Hahn, F Rumpf, B 71, 2141 (1938)

---

PART 4

3-hydroxy-4-ethoxybenzaldehyde, 18, [1]
4-hydroxy-3-methoxybenzaldehyde (vanillin), 95, [2-5]
4-hydroxy-3-ethoxybenzaldehyde, 75, [4]
2,3-dimethoxybenzaldehyde, 60, [4]
2,3-diethoxybenzaldehyde, 59, [1]
2,4-dimethoxybenzaldehyde, *, [3,13]
2,4-diethoxybenzaldehyde, *, [14]
3,4-dimethoxybenzaldehyde, 80, [4,15-19]
2,5-dimethoxybenzaldehyde, *, [20,21]
3,4-methylenedioxybenzaldehyde (piperonal), 75, [2,7,15,19,22-26]
3-methoxy-4-benzyloxybenzaldehyde, 97, [27-31]
4-methoxy-3-benzyloxybenzaldehyde, 88, [16,30]

[1] A Dornow, G Petsch, Ar 284, 153 (1951)
[2] M Koremura, H Oku, T Shono, T Nakanishi, Takamine Kenkyusho Nempo 13, 205 (1961) [CA 57.16450 (1962)]
[3] MGS Rao, C Srikantia, MS Iyengar, Helv 12, 581 (1929)
[4] CB Gairaud, GR Lappin, J Org Chem 18, 1 (1953)
[5] G Hahn, K Stiehl, B 71, 2154 (1938)
[6] DE Worrall, Am Soc 56, 1556 (1934)
[7] E Knoevenagel, L Walter, B 37, 4502 (1904)
[8] KW Rosenmund, B 46, 1034 (1913)
[9] R Stewart, RH Clark, Canad J Res 26B, 7 (1948)
[10] ON Tolkachev, VG Voronin, NA Preobrazhenskii, Z obsc Chim 28, 3320 (1958) [CA 53.14029 (1959)]
[11] DE247817
[12] SP Makarow, J pr 141, 77 (1934)
[13] C Mannich, M Falber, Ar 267, 601 (1929); C (1930) I, 77
[14] JR Merchant, AJ Mountwala, J Org Chem 23, 1774 (1958)
[15] KH Slotta, G Haberland, Ang Ch 46, 766 (1933)
[16] R Robinson, S Sugasawa, Soc (1931) 3163
[17] H Kondo, T Kondo, J Pharm Soc Japan 48, 56 (1927); C (928) II, 55
[18] G Barger, J Eisenbrand, L Eisenbrand, E Schlittler, B 66, 450 (1933)
[19] KW Rosenmund, B 43, 3412 (1910)
[20] FGP Remfry, Soc 99, 282 (1911)
[21] S Sugasawa, H Shigehara, B 74, 459 (1941)
[22] L Bouveault, A Wahl, CR 135, 41 (1902); C (1902) II, 449
[23] P Medinger, M 27, 238 (1906)
[24] L Bouveault, A Wahl, Bl [3] 29, 521 (1903)
[25] Y Tanaka, T Midzuno, J Pharm Soc Japan 49, 47 (1929); C (1929) I, 2978
[26] PW Neber, A Burgard, W Thier, A 526, 277 (1936)
[27] NA Lange, WE Hambourger, Am Soc 53, 3865 (1936)
[28] M Tomita, H Watanabe, J Pharm Soc Japan 58, 223 (1938); C (1939) I, 1978
[29] S Kobayashi, S P In phys chem Res 6, 149 (1927); C (1928) I, 1026
[30] E Spaeth, A Orechoff, F Kuffner, B 67, 1214 (1934)
[31] H Kondo e.a., Itsuu Kenkyusho Nempo 9, 1 (1958) [CA 54.1399 (1960)]

[GC_MS]

Format: precursor, yield, reference(s)

PART 5

4-methoxy-2-ethoxybenzaldehyde, *, [1,2]
3-methoxy-4-ethoxybenzaldehyde, 85, [3-7]
4-methoxy-3-ethoxybenzaldehyde, 64, [3,6,8]
3-methoxy-2-propyloxybenzaldehyde, 27, [9]
3-methoxy-2-isopropyloxybenzaldehyde, 29, [9]
3-methoxy-2-butyloxybenzaldehyde, 20, [9]
3-methoxy-2-pentyloxybenzaldehyde, 57, [9]
3-methoxy-2-(3-methylbutyloxy)-benzaldehyde, 43, [9]
3-ethoxy-2-isopropyloxybenzaldehyde, 52, [9]
3-ethoxy-2-butyloxybenzaldehyde, 66, [9]
3-ethoxy-2-pentyloxybenzaldehyde, 47, [9]
3,4-dibenzyloxybenzaldehyde, *, [8]
3-nitro-2-hydroxybenzaldehyde, *, [10]
3-nitro-4-methoxybenzaldehyde, 74, [10-12]
3-nitro-4-hydroxybenzaldehyde, *, [12]
2-nitro-3-methoxybenzaldehyde, 85, [13]
2-nitro-4-methoxybenzaldehyde, 70, [13]
2-nitro-5-methoxybenzaldehyde, 80, [13]
2-nitro-5-acetoxybenzaldehyde, quant, [14]

[1] MGS Rao, C Srikantia, MS Iyengar, Helv 12, 581 (1929)
[2] JR Merchant, AJ Mountwala, J Org Chem 23, 1774 (1958)
[3] E Spaeth, A Dobrowsky, B 58, 1274 (1934)
[4] T Kondo, K Shinozaki, K Ishi, J Pharm Soc Japan 48, 169 (1928); C (1929) I, 1112
[5] K Sawai, J Pharm Soc Japan 49, 260 (1929); C (1929) I, 2749
[6] A Dornow, G Petsch, Ar 284, 153 (1951)
[7] KW Bentley, SF Dyke, J Org Chem 22, 429 (1957)
[8] JR Merchant, SR Agrawal, J Indian Chem Soc 40, 472 (1963) [CA 59.9846 (1963)]
[9] E Profft, Arzneimittel-Forsch 9, 157 (1959)
[10] FGP Remfry, Soc 99, 282 (1911)
[11] KH Slotta, G Szyszka, B 68, 184 (1935)
[12] JP26960 [CA 62.14569 (1965)]
[13] GS Sidhu, PB Sattur, SJ Hasan, J Sci Ind Research (India) 19C, 38 (1960) [CA 55.15381 (1961)]
[14] RJS Beer, K Clarke, HG Khorana, A Robertson, Soc (1948) 1605

---

PART 6

6-nitro-2-acetoxybenzaldehyde, quant, [1]
2-nitro-4-methylbenzaldehyde, 65, [2]
4-methoxy-3-rhodanbenzaldehyde, *, [3]
2-iodo-3-methoxybenzaldehyde, 75, [2]
2-hydroxy-3-carboxybenzaldehyde, *, [4]
5-bromo-2,3-dimethoxybenzaldehyde, 90, [5,6]
3,5-dibromo-4-hydroxybenzaldehyde, *, [3]
4,5-dimethoxy-2-methylbenzaldehyde, *, [7]
4,5-dimethoxy-2-ethylbenzaldehyde, *, [7]
2,4-dimethoxy-3-methylbenzaldehyde, *, [7]
2,4-dimethoxy-3-ethylbenzaldehyde, *, [7]
4,6-dimethoxy-2-methylbenzaldehyde, *, [5]
2,4-diethoxy-3-methylbenzaldehyde, *, [7]
4,6-diethoxy-2-methylbenzaldehyde, *, [5]
2-methoxy-3,5-dimethylbenzaldehyde, *, [7]
2-methoxy-4,5-dimethylbenzaldehyde, *, [7]
2,4-dimethoxy-3-benzylbenzaldehyde, *, [7]
2,4-diethoxy-3-benzylbenzaldehyde, *, [7]
4-methoxy-6-ethoxy-2-methylbenzaldehyde, *, [5]
4-methoxy-2,6-dimethylbenzaldehyde, *, [5]
4-ethoxy-2,6-dimethylbenzaldehyde, *, [5]
6-methoxy-2,4-dimethylbenzaldehyde, *, [5]

[1] RJS Beer, K Clarke, HG Khorona, A Robertson, Soc (1948) 1695
[2] GS Sidhu, PB Sattur, SJ Hasan, J Sci Ind Research (India) 19C, 38 (1960) [CA 55.15381 (1961)]
[3] JP26960 [CA 62.14569 (1965)]
[4] FGP Remfry, Soc 99, 282 (1911)
[5] JR Merchant, AJ Mountwala, J Org Chem 23, 1774 (1958)
[6] VG Voronin, GD Kulikovskaya, LD Magda, Z Org Chim 1,719 (1965) [CA 63.5546 (1965)]
[7] JR Merchant, SR Agrawal, J Indian Chem Soc 40, 472 (1963) [CA 59.9846 (1963)]

---

PART 7

6-ethoxy-2,4-dimethylbenzaldehyde, *, [1]
4-hydroxy-3,5-dimethoxybenzaldehyde, 97, [2,3]
2,3,4-trimethoxybenzaldehyde, 73, [4]
2,3,5-trimethoxybenzaldehyde, *, [1]
2,4,5-trimethoxybenzaldehyde, *, [5]
3,4,5-trimethoxybenzaldehyde, 78, [2,4,6,7]
3,4,5-triethoxybenzaldehyde, 55, [4]
3,5-dimethoxy-4-ethoxybenzaldehyde, 65, [3]
5-bromo-2-hydroxy-3-methoxybenzaldehyde, *, [8]
5-iodo-2-hydroxy-3-methoxybenzaldehyde, 26, [8]
5-bromo-4-hydroxy-3-methoxybenzaldehyde, *, [9,10]
2-bromo-3,4-dimethoxybenzaldehyde, 77, [11]
5-bromo-3,4-dimethoxybenzaldehyde, 50, [12]
                "                , 80, [13] (different MP)
5-iodo-2,3-dimethoxybenzaldehyde, *, [8]
5-nitro-3,4-dimethoxybenzaldehyde, *, [7]
5-nitro-2,4-dimethoxybenzaldehyde, *, [14]
4-methoxy-2,3,6-trimethylbenzaldehyde, *, [15]
2,5-dimethoxy-3,4-methylenedioxybenzaldehyde, *, [16]

[1] JR Merchant, AJ Mountwala, J Org Chem 23, 1774 (1958)
[2] F Mauthner, J pr [2] 92, 194 (1915)
[3] F Benington, RD Morin, LC Clarke, Am Soc 76, 5555 (1954)
[4] KH Slotta, G Szyszka, J pr [2] 137, 339 (1933)
[5] MPJM Jansen, R 50, 291 (1931)
[6] E Spaeth, M 40, 129 (1919)
[7] KH Slotta, G Szyszka, B 98, 184 (1935)
[8] E Profft, M Pannach, Ar 299, 633 (1966)
[9] ON Tolkachev, VG Voronin, NA Preobrazhenskii, Z Obsc Chim 28, 3320 (1958) [CA 53.14029 (1959)]
[10] SP Makarow, J pr 141, 77 (1934)
[11] K Bessho, Chem Pharm Bull (Tokyo) 11, 1491 (1963)
[12] M Tomita, H Watanabe, J Pharm Soc Japan 58, 223 (1938)
[13] H Kondo e.a, Itsuu Kenkyusho Nempo 9, 1 (1958) [CA 54.1399 (1960)]
[14] MGS Rao, C Srikantia, MS Iyengar, Helv 12, 581 (1929)
[15] JR Merchant, SR Agrawal, J Indian Chem Soc 40, 472 (1963) [CA 59.9846 (1963)]
[16] Mannich, M Falber, Ar 267, 601 (1929); C (1930) I, 77

[GC_MS]

Format: precursor, yield, reference(s)

PART 1

benzaldehyde, 85, [5-10]
4-methylbenzaldehyde, 38, [10]
4-trifluoromethylbenzaldehyde, 55, [11]
2-chlorobenzaldehyde, 66, [10,12]
3-chlorobenzaldehyde, 53, [10]
4-chlorobenzaldehyde, 76, [10]
4-hydroxybenzaldehyde, 35, [9,10,12]
2-methoxybenzaldehyde, 91, [13]
3-methoxybenzaldehyde, 54, [12]
4-methoxybenzaldehyde, 60, [6,7,9,10,12,14]
2-ethoxybenzaldehyde, 73, [12]

[5] B Priebs, A 225, 319 (1884); DE Worrall, Org Synth Coll Vol 1, 405 (1932)
[6] E Knoevenagel, L Walter, B 37, 4502 (1904)
[7] GA Alles, Am Soc 54, 271 (1932)
[8] HB Hass, AG Susie, RL Heider, J Org Chem 15, 8 (1950)
[9] CB Gairaud, GR Lappin, J Org Chem 18, 1 (1953)
[10] M Koremura e.a., Takamine Kenkyusho Nempo 13, 212 (1961) [CA 57.16451 (1962)]
[11] GB870541; US3117160
[12] O Schales, HA Graefe, Am Soc 74, 4486 (1952)
[13] GB671240
[14] FW Hoover, HB Hass, J Org Chem 12, 501 (1947)

---

PART 2

2-nitrobenzaldehyde, 46, [1]
         "         , 62, [1] (different MP)
3-nitrobenzaldehyde, 12, [1]
4-nitrobenzaldehyde, 55, [1,2]
4-aminosulfonbenzaldehyde, *, [3]
4-diethylaminobenzaldehyde, 18, [2]
4-acetaminobenzaldehyde, 30, [2]
2,4-dichlorobenzaldehyde, 73, [2]
3,4-dichlorobenzaldehyde, 52, [2]
4-methoxy-3-chloromethylbenzaldehyde, 78, [1]
2-hydroxy-3-methoxybenzaldehyde, 45, [2,4]
4-hydroxy-3-methoxybenzaldehyde, 72, [1,4-6]
3-methoxy-4-benzoyloxybenzaldehyde, 72, [5]
4-hydroxy-3-ethoxybenzaldehyde, 50, [4]
2,3-dimethoxybenzaldehyde, 79, [2,4]
3,4-dimethoxybenzaldehyde, 35, [4,7]
3,4-methylenedioxybenzaldehyde (piperonal), 80, [1,8]
3-methoxy-2-propyloxybenzaldehyde, 71, [9]

[1] M Koremura e.a., Takamine Kenkyusho Nempo 13, 212 (1961) [CA 57.16451 (1962)]
[2] O Schales, HA Graefe, Am Soc 74, 4486 (1952)
[3] JP17017 [CA 60.13184 (1964)]
[4] CB Gairaud, GR Lappin, J Org Chem 18, 1 (1953)
[5] R Stewart, RH Clark, Canad J Res 26B, 7 (1948)
[6] LV Fennoy, J Org Chem 26, 4696 (1961)
[7] GA Alles, Am Soc 54, 271 (1932)
[8] E Knoevenagel, L Walter, B 37, 4502 (1904)
[9] E Profft, Arzneimittel-Forsch 9, 157 (1959)

---

PART 3

3-methoxy-2-isopropoxybenzaldehyde, 67, [1]
3-methoxy-2-butyloxybenzaldehyde, 53, [1]
3-methoxy-2-(2-methylpropyloxy)-benzaldehyde, 57, [1]
3-methoxy-2-pentyloxybenzaldehyde, 48, [1]
3-methoxy-2-(3-methylbutyloxy)-benzaldehyde, 48, [1]
3-methoxy-2-hexyloxybenzaldehyde, 64, [1]
3-methoxy-2-octyloxybenzaldehyde, 63, [1]
2-methoxy-3-ethoxybenzaldehyde, 31, [1]
3-ethoxy-2-propyloxybenzaldehyde, 51, [1]
3-ethoxy-2-isopropyloxybenzaldehyde, 62, [1]
3-ethoxy-2-butyloxybenzaldehyde, 60, [1]
3-ethoxy-2-(2-methylpropyloxy)-benzaldehyde, 62, [1]
3-ethoxy-2-pentyloxybenzaldehyde, 46, [1]
3-ethoxy-2-(3-methylbutyloxy)-benzaldehyde, 57, [1]
3-ethoxy-2-octyloxybenzaldehyde, 69, [1]
3-ethoxy-2-dodecyloxybenzaldehyde, 77, [1]
2-nitro-5-acetoxybenzaldehyde, *, [2]
5-bromo-2-hydroxy-3-methoxybenzaldehyde, *, [3]

[1] E Profft, Arzneimittel-Forsch 9, 157 (1959)
[2] RJS Beer, K Clark, HG Khorana, A Robertson, Soc (1948), 1605
[3] E Profft, M Pannach, Ar 299, 633 (1966)

[GC_MS]

Format: precursor, yield, reference(s)

PART 1

benzaldehyde, 70, [1-3]
2-chlorobenzaldehyde, 68, [3]
3-chlorobenzaldehyde, 36, [3]
4-chlorobenzaldehyde, 7, [3]
3-nitrobenzaldehyde, 62, [3]
4-nitrobenzaldehyde, 10, [3]
4-methylbenzaldehyde, 34, [3]
4-hydroxybenzaldehyde, 22, [3]
4-methoxybenzaldehyde, 90, [1,3]
4-hydroxy-3-methoxybenzaldehyde, 54, [3-5]
3,4-methylenedioxybenzaldehyde (piperonal), 48, [3]
3-methoxy-4-benzoyloxybenzaldehyde, *, [4]
3-methoxy-2-propyloxybenzaldehyde, 50, [6]
3-methoxy-2-isopropyloxybenzaldehyde, 21, [6]
3-methoxy-2-butyloxybenzaldehyde, 36, [6]
3-methoxy-2-(2-methylpropyloxy)-benzaldehyde, 34, [6]
3-methoxy-2-pentyloxybenzaldehyde, 26, [6]

[1] HB Hass, AG Susie, RL Heider, J Org Chem 15, 8 (1950)
[2] PC Ferreira, LA de Pontes, Anais fac farm e odontol univ Sao Paulo 12, 1 (1954) [CA 50.10667 (1956)]
[3] M Koremura, J agr chem Soc Japan 36, 552 (1962) [CA 62.3962 (1965)]
[4] R Stewart, RH Clark, Canad J Res 26B, 7 (1948)
[5] CB Gairaud, GR Lappin, J Org Chem 18, 1 (1953)
[6] E Profft, Arzneimittel-Forsch 9, 157 (1959)

---

PART 2

3-methoxy-2-(3-methylbutyloxy)-benzaldehyde, 39, [1]
3-methoxy-2-nonyloxybenzaldehyde, 36, [1]
3-ethoxy-2-isopropyloxybenzaldehyde, 14, [1]
3-ethoxy-2-hexyloxybenzaldehyde, 37, [1]
3-ethoxy-2-nonyloxybenzaldehyde, 31, [1]
[...]
3-nitro-4-hydroxybenzaldehyde, 50, [5]
3-nitro-4-methoxybenzaldehyde, 40, [5]
3,5-dichloro-4-hydroxybenzaldehyde, 40, [5]

[1] E Profft, Arzneimittel-Forsch 9, 157 (1959)
[5] JP26960 [CA 62.14569 (1965)]

[GC_MS]

Format: precursor, yield, reference(s)

PART 1

benzaldehyde, 65-70, [2,6]
4-chlorobenzaldehyde, 86, [6]
3-chlorobenzaldehyde, 52, [6]
2-chlorobenzaldehyde, 77, [6]
4-nitrobenzaldehyde, 47, [6]
3-nitrobenzaldehyde, 31, [6]

[2] HB Hass, AG Susie, RL Heider, J Org Chem 15, 8 (1950)
[6] M Koremura, J agr chem Soc Japan 36, 552 (1962) [CA 62.3962 (1965)]

---

PART 2

2-nitrobenzaldehyde, 47, [1]
4-methylbenzaldehyde, 52, [1]
4-methoxybenzaldehyde, 90, [1,2]
4-hydroxybenzaldehyde, 22, [1]
4-hydroxy-3-methoxybenzaldehyde, 23, [1]
3,4-methylenedioxybenzaldehyde (piperonal), 36, [1]
3-thiocyanobenzaldehyde, 40, [3]
4-thiocyanobenzaldehyde, 39, [3]

[1] M Koremura, J agr chem Soc Japan 36, 552 (1962) [CA 62.3962 (1965)]
[2] HB Hass, AG Susie, RL Heider, J Org Chem 15, 8 (1950)
[3] JP19155 [CA 62.7684 (1965)]

[Rhodium]

Great! I'm in the process of converting it to HTML and placing it here:

https://www.thevespiary.org/rhodium/Rhodium/chemistry/nitrostyrene.references.html

The nitromethane section is still missing, and I will add it to the document tomorrow and also put <strong> tags around all the square brackets to make the refs more distinct, as in "Part 2" of the nitrobutane section.

[GC_MS]

Once you know how to deal with the Houben-Weyl, it is one of the most valuable works I'm aware of, chemistry wise. It contains many "general procedures", but what I find most interesting is the fact that it gives a good overview of reaction possibilities. For instance, the reduction of amines. Houben-Weyl doesn't list that many direct amphetamine-related reductions, but it gives a very good overview of what functional groups can be reduced to amines, and what kind of chemicals can be used to achieve that reduction. As such, I have often found it a very good starting point.

[Aurelius]

the 'strong' tags should be used in place of 'b' at the hive?  or does it really matter?

[GC_MS]

the 'strong' tags should be used in place of 'b' at the hive?  or does it really matter?

Hmmm, isn't <strong> intended for Rh's HTML?

[Rhodium]

Yup, I'm talking about my own HTML, the Hive markup only supports the tag at the moment.

[roger2003]

The ref. literature (in

Post 404813

(GC_MS: "benzaldehydes + nitromethane pt 1", Methods Discourse)) :

[1] B Priebs, A 225, 319 (1884); DE Worrall, Org Synth Coll Vol I, 405 (1932)

must be changed to:

Org Synth C V 1, 413