4-Hydroxybenzyl Alcohol → HCID 131720747, compound

Participants

Reaction Steps

Sodium methoxide (4.17 g, 73.4 mmole) was added under argon to a solution of 4-hydroxybenzyl alcohol (8.67 g, 69.9 mmol) in dry DMF (70 mL) and the reaction mixture was stirred for 30 minutes at room temperature. 4-Bromophenyldimethylsilylmethyl-bromide (22.6 g, 73.4 mmol) was added through a canula and the reaction was stirred at RT for 30 minutes and at 65° C. for 45 minutes. The reaction was poured into ice water (250 mL) and extracted with ethyl acetate. The combined extracts were washed with water, 5% sodium bicarbonate and brine and the dried (Na2 SO4). The solution was concentrated to an oil at reduced pressure and purified by flash chromatography (silica gel, 20% ethyl acetate/hexane) to yield the product as a clear, colorless oil (9.23 g, 38%). 1H NMR (400 MHz, CDCl3) 7.48 (dd, 4H), 7.10 (dd, 4H), 4.61 (s, 2H), 3.77 (s, 2H), 0.42 (s, 6H).

Provenance & Evidence