3-Hydroxybenzyl alcohol → 3-(2-Propyn-1-yloxy)benzenemethanol

To an aqueous solution of 3-hydroxybenzyl alcohol (2.00 g, 16.1 mmol) in sodium hydroxide (35 mL, 1.5 M) was added propargyl bromide (2.11 g, 17.7 mmol), and the mixture was stirred at room temperature for 24 hours. The reaction mixture was extracted with diethyl ether and washed with a 1.5 M aqueous sodium hydroxide solution and saturated brine, and the organic layer was concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=5:5) to give the title compound (0.82 g, yield 31%) as an oily matter.

1. extractionThe reaction mixture was extracted with diethyl ether
2. washwashed with a 1.5 M aqueous sodium hydroxide solution and saturated brine
3. concentrationthe organic layer was concentrated under reduced pressure
4. customThe resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=5:5)

ORD record

ord-4819e5b250314cac8a65953c3b539ac9

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08008525B2