Synthesis of 4,5-dimethylchrysene.
Newman, Melvin S.
J. Am. Chem. Soc. (1940), 62 2295-300.
Abstract
Details are given of the prepn. of o-MeC6H4CH2OH in 42% yield from PhCH2Cl and trioxymethylene or in 55% yield from o-MeC6H4MgBr; SOCl2 gives 89% of o-MeC6H4CH2Cl; NaCN in dil. EtOH gives 86% of o-MeC6H4CH2CN (I). PhMgBr and propylene oxide give 60% of PhCH2CHMeOH which with PBr3 yields 63% of PhCH2CHMeBr (II).
Retentive Friedel-Crafts alkylation of benzene with optically active 2-chloro-1-phenylpropane and 1-chloro-2-phenylpropane.
Masuda, Shinji; Nakajima, Tadashi; Suga, Sohei.
Bull. Chem. Soc. Jpn. (1983), 56(4), 1089-94. (In English)
They prepare 1-phenyl-2-propanol from propylene oxide and benzene.
Process for production of 1-phenyl-2-propanol.
Mamedov, Markaz K.; Gusejnov, Vidadi M. (USSR).
U.S.S.R. (1992), SU 1778109 Patent in Russian.
Abstract
PhCH2CHMeOH prodn. by adding C6H6 to propylene oxide (I) in the presence of AlCl3 at 5-6° and passing an inert gas through the reaction mixt. was improved to increase the yield and improved the product quality by carrying out the process with 5-6:3:1 C6H6-I-AlCl3 and by using 2 L/min He as the inert gas.
Patent US5223633 (http://l2.espacenet.com/dips/viewer?PN=US5223633&CY=gb&LG=en&DB=EPD)
This has some complex method of making 1-phenyl-2-propanol which is probably more applicable to more valuable products.
Grignard reactions of phenyloxirane in the presence of titanium tetraisopropoxide.
Sosnovskii, G. M.; Astapovich, I. V.
Zh. Org. Khim. (1992), 28(7), 1377-9.
Abstract
The title reactions gave PhCHXCH2OH (X = Cl, Br, iodo) and HOCHPhCH2I in £90% combined yield after 20 min, and 65-80% PhCH2CHROH (R = Me, Et, Ph) after 6 h.(They are reacting with grignard reagents)
More to come....
Foxy
Those who give up essential liberties for temporary safety deserve neither liberty nor safety
This should work, although the yeild doesn't seem to bee stellar.
Foxy
Patent US4396627 (http://l2.espacenet.com/dips/viewer?PN=US4396627&CY=gb&LG=en&DB=EPD)
5. 1-(4-Acetylphenyl) propan-2-one
Chromic acid solution (11.5 ml, made by adding sulphuric acid [7.3 ml] to sodium dichromate [10.0 g] in water [30 ml] and making up to 50 ml with water) was added to a vigorously stirred solution of 1-(4-acetylphenyl) propan-2-ol (3.8 g) in ether (50 ml) keeping between 25 DEG-30 DEG. The mixture was stirred at ambient temperature for 2 hours, the organic phase was separated, washed with sodium bicarbonate solution and with saturated sodium chloride solution. The dried (MgSO4) solution was evaporated and distilled (2.5 g). b.p. 122 DEG-128 DEG/0.1 mm.
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