Hydrochloric Acid → (S)-1,1,3,4,4,6-hexamethyl1,2,3,4-tetrahydronaphthalene

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To a suspension of lithium aluminum hydride (9.56 g; 0.252 mol) in tetrahydrofuran (70 ml) under a nitrogen stream, a solution of (S)-3-chloromethyl-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene ([α]546 26.1° (C=1 in n-hexane)) (62.9 g; 0.251 mol) in tetrahydrofuran was dropwise added. After refluxing for 15 hours, the reaction mixture was treated with aqueous tetrahydrofuran in nitrogen, admixed with 5% hydrochloric acid (600 ml) and extracted with n-hexane. The extract was washed with saturated sodium chloride solution, dried, concentrated and distilled to give (S)-1,1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene (46.0 g; 0.213 mol; 85%). [α]546 -49.1° (C=1 in chloroform). B.P., 91° C./0.5 mmHg.

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