Water → HCID 10560064, compound

Participants

Reaction Steps

4.00 g of 4-chloro-2-hydroxybenzyl alcohol [prepared as described in step (a) above] were dissolved in 80 ml of N,N-dimethylacetamide, and then 2.83 g of potassium t-butoxide were added to the resulting solution, whilst ice-cooling, and the mixture was stirred for 10 minutes. 2.09 ml of methoxymethyl chloride were then added to the reaction mixture, whilst ice-cooling, and the mixture was then stirred at room temperature for 1 hour. At the end of this time, 60 ml of water and 300 ml of ethyl acetate were added, and the ethyl acetate layer was separated and washed with a saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate. It was then concentrated by evaporation under reduced pressure. The residue was purified by silica gel column chromatography, using a 2:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 4.69 g (yield 92%) of the title compound as an oily substance.

Provenance & Evidence