Ethyl bromoacetate → Ethyl 2,4-dibenzyloxyphenoxyacetate

Participants

Reaction Steps

A mixture of 2,4-dibenzyloxyphenol (3.1 g) and sodium hydride (0.44 g, 60% dispersion in mineral oil) in THF (75 mL) is refluxed for 30 minutes then refluxing is allowed to abate. Neat ethyl bromoacetate (1.8 g) is added and refluxing continued for 1 hour. The reaction is concentrated in vacuo and the residue partitioned between ethyl acetate (100 mL) and water (100 mL). The organic phase is washed with water (100 mL), dried o ver magnesium sulphate, filtered and concentrated in vacuo to give a light brown oil. Flash chromatography of the residue eluting with dichloromethane affords ethyl 2,4-dibenzyloxyphenoxyacetate (3.2 g) after trituration with pentane.

Provenance & Evidence