公开(公告)号：DE4407464A1

公开(公告)日：1995-09-28

申请号：DE4407464

申请日：1994-03-07

Applicant: BASF AG

Inventor： JOHN MICHAEL DR ,  RHEUDE UDO DR ,  PAUST JOACHIM DR ,  MEYSER JOACHIM DR

IPC: C07C29/32 ,  C07C29/40 ,  C07C35/17 ,  C07C35/18 ,  C07C43/184 ,  C07C43/188 ,  C07C45/58 ,  C07C49/337 ,  C07C49/35 ,  C07C49/537 ,  C07C49/577 ,  C07C67/293 ,  C07C69/78 ,  C07C69/96 ,  C07D303/14 ,  C07D303/16 ,  C07D303/22 ,  C07D309/12 ,  C07D407/12 ,  C07F7/18 ,  C07C49/297 ,  C07C45/00 ,  C07D303/02

Abstract: Prodn. of 1,2,2-trimethyl- cyclopentylmethylketone derivs. of formula (I) comprises (A) (i) reacting a 2,2,6-tri- methyl-cyclohexane-1-one of formula (II) with a methylcarbanion of formula CH3 M (III) and converting the resulting 1,4-dihydroxy-1,2,2,6-tetramethylcyclohexane deriv. of formula (IV) into a mixt. of the corresp. cpds. (V) and (VI) by acid catalysed elimination of the tert. hydroxyl gp., or (A) (ii) the 2,2,6-trimethylcyclohexane-1-one cpd. (II) may be converted directly into the cpd. (VI) by a Wittig reaction with a triphenylmethylenephosphorane cpd. of formula (C6H5)3P=CH2 (VII); (B) converting the cpd. (VI) into the cpd. (V) by acid catalysed isomerisation of the double bond; (C) epoxidising the double bond in the cpd. (V) in the known way by reacting with peroxyacids, their salts or hydroperoxides to form the 7-oxa-bicycloÄ4.1.0Üheptane cpd. of formula (VIII) and (D) converting the cpd. (VIII) into the 1,2,2-tri- methyl-cyclopentylmethylketone cpd. (I) by reaction with Lewis acids and opt. splitting off the protective gp. from the O atom. R=H, alkyl, aryl, arylmethyl, trialkylsilyl, triarylsilyl, alkylarylsilyl, alkyloxyalkyl, tetrahydropyranyl, arylmethyloxycarbonyl, alkanoyl or benzoyl residue; M =Li, MgCl, MgBr or MgI.