Sodium Hydroxide → 2-{2-[(3-Methyloxiran-2-yl)methoxy]phenyl}ethan-1-ol

A mixture of 5.04 g (0.033 mole) of 2-(2-hydroxyethyl)-3-methylphenol, 1.33 g (0.033 mole) of sodium hydroxide in 135 ml of water, and 5.00 g (0.033 mmole) of erythro-(1-bromoethyl)oxirane in 25 ml of 1,2-dimethoxyethane was stirred at room temperature for about 72 hours. The mixture was extracted with 5×100 ml of ether. The extract was washed with dilute sodium hydroxide solution, dilute brine and saturated brine, dried over MgSO4 and concentrated in vacuo to give 4.25 g (58%) of 2-methyl-3-[2-(2-hydroxyethyl)phenoxymethyl]oxirane. A 1:1 (v/v) mixture of 1-methylethylamine and water (130 ml) was added to the oxirane and the mixture was heated at reflux for 5 hours, and concentrated in vacuo to dryness. The residue was dissolved in ether, dried over MgSO4 and concentrated to dryness to give 2.90 g of oil. The oil was flash chromatographed on a silica gel column by elution with 3% CH3OH in CHCl3 saturated with ammonia gas to give 0.5 g of product. Conversion to the oxalate salt gave material with m.p. 138°-140° C. (0.5 isopropanol solvate).

1. extractionThe mixture was extracted with 5×100 ml of ether
2. washThe extract was washed with dilute sodium hydroxide solution, dilute brine and saturated brine
3. dry with materialdried over MgSO4
4. concentrationconcentrated in vacuo

ORD record

ord-81c4cbe4be7c4305ba25dd205c714b6d

Source dataset

uspto-grants-1990_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04945182