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Methodes d'acces AU methanol ‐ D 4
Author(s) -
Ahmadi Ahmad,
Herbert Michel,
Pichat Louis
Publication year - 1972
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590080105
Subject(s) - chemistry , methanol , yield (engineering) , acetic acid , acetic anhydride , bromine , solvent , bromide , acetyl chloride , inorganic chemistry , medicinal chemistry , nuclear chemistry , organic chemistry , catalysis , materials science , metallurgy
Abstract Simple methods for the preparation of methanol D 4 have been explored. The “carboxy‐inversion” reaction has been applied to acetyle m‐chloroperoxybensoate, prepared with a 81% yield by action of m‐chloroperoxybenzoic acid with acetyl chloride. The carboxy inversion reaction yield is only 15%. This transposition is solvent dependent. When the solvent used is chlorinated e. g. C CL 4 , C CL 2 = C Cl 2 it participates in the reaction. The oxydation of acetic anhydride with iodine does not provide methyle acetate while the method is successfull with the higher homologues. A modification of the Hunsdiecker's method : e. g. action of bromine on acetic acid in presence of mercuric oxide provides methyl bromide with a 90% yield. Alcaline hydrolisis of the latter gives rise to methanol with a 60% yield. An exchange reaction between dimethylsul foxide D 6 and methanol OD in heavy water at 200°C in presences of NaOD has been briefly studied. CD 3 OD is obtained while a part of DMSO D 6 is reduced into dimethyl sulfide.