Hydrochloric Acid → 4-[[4-(3-Hydroxypropyl)phenyl](3,3,5,5-tetramethylcyclohexylidene)methyl]phenol

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-{4-[(4-hydroxyphenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}propanoate (169) (0.176 g, 0.43 mmol) in THF (10 mL) at 0° C. was added LAH (1 M in THF, 1.10 mL, 1.10 mmol) dropwise. The reaction mixture was stirred at 0° C. for 1 h, EtOAc (5 mL) was added, and stirring continued for 10 min. The mixture was then acidified to pH=2 with an aqueous solution of 1 N HCl, extracted with EtOAc (2×50 mL). The combined organic extract was washed with water, brine and dried (Na2SO4), filtered, and the filtrate was concentrated to give the crude product as white solid. The crude product was purified by flash chromatography on silica gel eluted with a gradient from hexanes to 40% EtOAc:hexanes to give a white residue, which upon trituration with hot hexanes containing 1% of MeOH yielded 0.15 g (92%) of compound 233 as a white solid. mp 160-161° C. 1H NMR (400 MHz, DMSO-d6): δ 0.85 (s, 6H), 0.86 (s, 6H), 1.23 (s, 2H), 1.60-1.70 (m, 2H), 1.86 (s, 2H), 1.88 (s, 2H), 2.53 (t, J=7.8 Hz, 2H), 3.35-3.40 (m, 2H), 4.42 (t, J=5.1 Hz, 1H), 6.64 (d, J=8.5 Hz, 2H), 6.89 (d, J=8.5 Hz, 2H), 6.99 (d, J=8.1 Hz, 2H), 7.07 (d, J=8.1 Hz, 2H), 9.23 (s, 1H). LCMS (ES): m/z 401 (M+Na)+, 377 (M−H)−.

Provenance & Evidence