Hydrochloric Acid → Acetyl hexamethyl tetralin, (S)-

Participants

Reaction Steps

To a solution of (S)-1,1,3,4,4,6-hexamethyl1,2,3,4-tetrahydronaphthalene ([α]546 -49.1° (C=1 in n-hexane)) (100.0 g; 0.463 mol) in 1,2-dichloroethane (300 g), acetyl chloride (38.0 g; 0.484 mol) and anhydrous aluminum chloride (71.0 g; 0.533 mol) were added, and the resultant mixture was stirred at 20° C. for 1 hour. The reaction mixture was treated with 10% hydrochloric acid (300 ml) and then separated into a water layer and an organic layer. The organic layer was washed with dilute hydrochloric acid and saturated sodium carbonate solution, dried and concentrated to give (S)-7-acetyl-1,1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene (107.5 g; 0.417 mol; 90%). B.P., 109° C./0.2 mmHg. [α]546 -36.9° (C=1 in ethanol).

Provenance & Evidence