Toluene → 3-(4,4-Dimethyl-cyclohex-1-enyl)-propan-1-ol

Participants

Reaction Steps

3-(4,4-Dimethyl-cyclohex-1-enyl)-propionic acid butyl ester (277.0 g, 1.10 mol, purity: 95%), toluene (140 g) and diethylacetate zinc complex (13.85 g, 5% w/w ester) were charged in a 2 1 reactor. The pot temperature was risen to 105° C. and PMHS (Polymethylhydroxysilane, 149.0 g, 2.48 mol) was introduced over the course of 3 hours. Stirring was continued for 1 hour and then the pot temperature was decreased to 40° C. The reaction mixture was put in a dropping funnel and the 2 1 reactor charged with 45% w/w aqueous KOH (403 g, 3.23 mol) and methanol (64.0 g). The pot temperature was risen to 60° C. and the reaction mixture was introduced over 30 minutes. Stirring was continued for 2 hours. The aqueous phase was separated and the organic phase washed with 5% w/w aqueous NaCl and twice with water. After concentration of the organic layer, the crude product was flash distilled (81° C., 1 hPa) to give 164.8 g of the desired alcohol (yield: 85%; GC purity: 96.2%).

Provenance & Evidence