1,1,4,4,7-pentamethyl-2,3-dihydronaphthalen-2-ol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4 g (18.3 mmol) of 3-methyl-6-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene in 20 mL of acetic acid was added 3.25 g (20.15 mmol) of bromine dropwise and the reaction was stirred at room temperature. After 16 hours, the reaction mixture was poured into brine and extracted with ethyl acetate. The organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (gradient elution with hexane-15% ethyl acetate/hexane) to give 6 g (97%) of 2-bromo-3-methyl-6-acetoxy -5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene.(M+=338). extracted with ethyl acetate The organic extracts were washed with brine dried over sodium sulfate concentrated under reduced pressure The residue was purified by flash chromatography (gradient elution with hexane-15% ethyl acetate/hexane)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 10 g (46.2 mmol) of 1,1,4,4,7-pentamenthyl-2-tetralone in 100 mL of ethyl alcohol was added 7 g (185 mmol) of sodium borohydride portionwise over 15 minutes. After the addition was complete the reaction was stirred at room temperature. After 16 hours the reaction mixture was concentrated under reduced pressure and the residue was partitioned between water and ethyl acetate. The organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (gradient elution with 5-10% ethyl acetate/hexane), followed by crystallization from hexane to afford 4 g (40%) of 3-methyl-6-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene.(M+=218). After the addition After 16 hours the reaction mixture was concentrated under reduced pressure the residue was partitioned between water and ethyl acetate The organic extracts were washed with brine dried over sodium sulfate concentrated under reduced pressure The residue was purified by flash chromatography (gradient elution with 5-10% ethyl acetate/hexane) followed by crystallization from hexane