Hydrochloric Acid → 1,1,2,4,4,6-Hexamethyl-1,2,3,4-tetrahydronaphthalene

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Reaction Steps

To a suspension of lithium aluminum hydride (6.5 g; 0.171 mol) in tetrahydrofuran in a nitrogen atmosphere, a solution of 2-chloromethyl-1,1,4,4,6-pentamethyl1,2,3,4-tetrahydronaphthalene (40.9 g; 0.163 mol) in tetrahydrofuran was added dropwise, and the resultant mixture was stirred at 70° C. for 15 hours. The reaction mixture was treated with aqueous tetrahydrofuran, dilute hydrochloric acid was added thereto, and the resultant mixture was extracted with n-hexane. The extract was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated to give 1,1,2,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene (31.6 g; 0.144 mol; 88%). B.P., 78° C./1.2 mmHg. M.P., 35°-36° C.

Provenance & Evidence