any positional isomer of phenylpropylamine + HI
conc. @ 275*C to give phenylpropane.
any positional isomer of phenylpropanol under the same conditions to give phenylpropane, allylbenzene and/or propenylbenzene. (products will depend on starting material).
Using concentration sulfuric (for acid-insensitive compounds) and Al metal for reduction of C=O an C-OH bonds to the respective C-H compound. (M. (1917), 38, 11)).
All ideas taken from one of PolytheneSam's image files (image of text from some book).
benzoyl chloride + Bicarb + MeCN + Ultrasound @ 45*C to give benzoic anhydride in 98% yield
Hu, Y; Wang, J.-X.; Li, S.;
Synth. Commun., (1997), 27, 243.
Maybe use this for higher yields in anhydride syntheses.
Benzyl bromide + NaNO
2 + AcOH + DMSO @ 35°C to give benzoic acid in 80% yield.
Matt. C.; Wagner, A.; Mioskiowski, C.
JOC, (1997), 62, 234.
Maybe use anti-markov on styrene, then this rxn to get phenylacetic acid.
Post 477828
(Rhodium: "Nitro and Bromide to COOH", Chemistry Discourse)
Benzaldehyde + FeCl
3/Zn + DMF/H
2, for 1 hour to give benzyl alcohol in 81% yield.
(also states that the reduction works for ketones)
Sadavarte, V.S.; Swami, S.S.; Dasai, D.G.
Synth. Commun., (1998), 28, 1139.
Maybe use this to reduce propiophenone to the alcohol- dehydrate to propenylbenzene-etc.
3-MeO-4-EtO-propenylbenzene is de-ethylated and de-methylated with KF on alumina in the microwave. 56% of the de-methylated product, 3% of the de-ethylated product.
Ousaid, A.; Thach, L.N.; Loupy, A.
Tet. Lett., (1997), 38, 2451.
Maybe use for de-methylation of eugenol.
Benzyl alcohol + clayfen, microwave, 5 seconds to give benzaldehyde in 92% yield.
(also works to oxidize 2° alcohols)
Varma, R.S.; Dahiya, R.
Tet. Lett. (1997), 38, 2043.
For the synth of benzaldehydes from their alcohols and P2Pol to P2P.
Benzyl alcohol + MnO
2-SiO
2 + microwave 20 seconds to give benzaldehyde in 88% yield.
Varma.
Tet. Lett. (1997), 38, 7823.
Again, synth of benzaldehyes.
Benzyl alcohol + K dichromate, benzene, water, @75°C for 8hr to give benzaldehyde in 86% yield.
Lon. J.-D.
J. Chem. Res.(S), (1997), 206.
Again, Benzaldehydes.
Piperonal + AmOAc/AcOH/MeOH/Ultrasound to give nitroethene
McNulty, J.; Steere, J.A.; Wolf, S.
Tet. Lett., (1998), 39, 8013.
