Ammonia → 3-Nitro-alpha-(trichloromethyl)benzenemethanol
Reaktionsgleichung
[OH-].[K+].[N+:3]([C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1C(O)=O)([O-:5])=[O:4].[N+](C(O)C1C=CC=CC=1)([O-])=O.[Cl:26][C:27]([C:30]([OH:40])([N+]([O-])=O)C1C=CC=CC=1)([Cl:29])[Cl:28].CC(C)([O-])C.[K+].N>>[Cl:26][C:27]([CH:30]([OH:40])[C:13]1[CH:12]=[CH:11][CH:7]=[C:6]([N+:3]([O-:5])=[O:4])[CH:14]=1)([Cl:29])[Cl:28]Komponenten
Versuchsvorschrift
Several articles have described the condensation of substituted benzaldehyde derivatives with chloroform in the presence of various bases to produce the corresponding α-(trichloromethyl)benzyl alcohols. In the case of nitrosubstituted benzaldehydes, only Cannizzaro reaction products are obtained when powdered potassium hydroxide is used as the base without solvent. Phase transfer conditions produce a mixture of nitrobenzoic acid, nitrobenzyl alcohol, and trichloromethylnitrobenzyl alcohol. Potassium t-butoxide in liquid ammonia at -75° C. has been reported to effect the desired condensation to form trichloromethyl-3-nitrobenzyl alcohol in 72% yield (Ya. G. Bal'on, V. E. Paranyuk, and M. D. Shul'man, Zh. Obsch. Khim., 44, 2633 (1974)). Under the same conditions potassium hydroxide or calcium oxide in dimethyl sulfoxide gives 5-10% lower yields. The generation of trichloromethide anion in solution from the decomposition of trichloroacetic acid in dimethyl sulfoxide has been used to prepare trichloromethyl-4-nitrobenzyl alcohol in 60% yield (P. J. Atkins et al., J. Chem. Soc., Chem. Comm., 1983, pp. 283-4).
Aufarbeitung
- customare obtained when
- customPhase transfer conditions produce
- customat -75° C.
- customcondensation
Quellen und Nachweise
- ORD-Eintrag
- ord-fc911c05710042329b4d4bc8d753bdd9
- Quelldatensatz
- uspto-grants-1986_07
- Patentnummer
- US04603227
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