Hydrochloric Acid → 3-Cyclopentyloxy-4-methoxybenzyl alcohol

Participants

Reaction Steps

1M lithium aluminum hydride in THF (1.5 mL) was added into a stirred solution of 3-cyclopentyloxy-4-methoxybenzaldehyde (1.1 g; 5 mmol) in THF solution in an ice bath. After the reaction was completed (as evidenced by TLC), the mixture was acidified with 2M HCl and extracted with ether. The organic phase was washed with water and dried over MgSO4. Filtration, followed by evaporation gave (3-cyclopentyloxy-4-methoxyphenyl)methanol as an oil ( 0.9 g; 81% yield; purity 98.1% by HPLC area). 1H-NMR: 6.92 (s, 1H), 6.88 (d, J=8.2 Hz, 1H), 6.84 (d, J=8.1 Hz, 1H), 4.80 (m, 1H), 4.61 (s, 2H), 3.84 (s, 3H), 2.13–1.78 (m, 6H), and 1.61 (s, 2H). 13C-NMR: 149.4, 147.6, 133.6, 119.3, 114.0, 111.7, 80.3, 60.5, 56.0, 32.7, and 24.0.

Provenance & Evidence