(S)-3-chloromethyl-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene → (S)-1,1,3,4,4,6-hexamethyl1,2,3,4-tetrahydronaphthalene

Participants

Reaction Steps

Into an autoclave, (S)-3-(chloromethyl)-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene 200 mg; 0.798 mmol), isopropanol (10 ml), sodium acetate trihydrate (120 mg; 0.882 mmol) and 10 % palladium carbon (160 mg) were charged, and the resultant mixture was stirred at 50° C. under a hydrogen pressure of 80 kg/cm2 for 12 hours. After cooling, the reaction mixture was filtered to separate palladium carbon, admixed with water and extracted with n-hexane. The extract was washed with saturated sodium hydrogen carbonate solution, dried and concentrated to give (S)-1,1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene (172 mg; 0.796 mmol).

Provenance & Evidence