(±)-1-(4-Hydroxy-3-methoxyphenyl)-4-methyl-3-pentanol

The discussion and purpose for the synthesis of this compound has been reported elsewhere [1]. To a cold (0°C) solution of 1-(4-hydroxy-3-methoxyphenyl)-4-methyl-3-pentanone (190 mg, 0.86 mmol) in EtOH (15 mL) was added sodium borohydride (40 mg, 1.1 mmol, 1.3 eq). The solution was stirred at 0°C for 30 min., then at room temperature for 1 h. 10% HCl (10 mL) was added and the solution was stirred at room temperature for 2 h. The solution was concentrated in vacuo and the aqueous residue was extracted with dichloromethane (3 x 10 mL). The organic fractions were combined, dried (MgSO₄) and the solvent was evaporated in vacuo. Chromatography on silica gel (40% EtOAc / hexanes) afforded a white solid (172 mg, 90%).

mp: 55-56°C.

IR (KBr) cm^-1: 3397 (OH).

¹H-NMR (CDCl₃) d: 0.92 (d, 6H, J=7.8 Hz, CH₃), 1.69 (m, 3H, H-2 and H-4), 2.59 (m, 1H, H-1a), 2.78 (m, 1H, H-1b), 3.40 (broad m, 1H, H-3), 3.88 (s, 3H, OCH₃), 5.47 (s, 1H, exchangeable with D₂O, OH), 6.72 (m, 2H, ArH-2 and ArH-6), 6.84 (d, 1H, J=8.7 Hz, ArH-5).

¹³C-NMR (CDCl₃) d: 17.4 (C-5a), 19.0 (C-5b), 32.4 (C-1), 33.9 (C-4), 36.4 (C-2), 56.1 (OCH₃), 76.4 (C-3), 111.2 (ArC-2), 114.5 (ArC-5), 121.1 (ArC-6), 134.5 (ArC-1), 143.8 (ArC-4), 146.6 (ArC-3).

MS m/e (rel %): 224 [M+] (83), 163 (44), 138 (62), 137 (100), 134 (44).

Anal. calc. for C₁₃H₂₀O₃: C 69.60, H 8.99; found: C 69.55, H 8.78.