Patent ID: 9725392
Date: 2017-08-08
CPC Classifications: C07C

Claim:
1. A method of making a compound of formula 1 wherein R is alkyl, cycloalkyl, alkenyl or alkynyl, said method comprising: a) reacting 2,6-dimethylphenol (VI) with potassium peroxymonosulfate and a catalytic amount of iodobenzene to produce 2,6-dimethylbenzoquinone (XVI); b) reacting 2,6-dimethylbenzoquinone (XVI) with ethylene glycol and a catalytic amount of p-toluenesulfonic acid to produce 2,6-dimethylbenzoquinone, mono ketal (VII); c) reacting 2,6-dimethylbenzoquinone, mono ketal (VII) with (Z)-3-methylpent-2-en-4-yn-1-ol (VIII), followed by reduction of the propargylic triple bond to provide allylic alcohol (X); d) reacting allylic alcohol (X) with MnO e) reacting quinol (XIII) with a carbanion magnesium halide, followed by ester hydrolysis to produce the compound of Formula 1.