Reaction #64769

Reaction equation

ethyl p-hydroxybenzoate

benzyl bromoacetate

K2CO3

→

title compound

Yield 99.0%

Ethyl 4-[2-Oxo-2-(phenylmethoxy)ethoxy]benzoate

Yield 99.0%

Solvents

DMF

water

Conditions

Workup

1. 1
   Extractionextracted with a 1:1 ether
2. 2
   WashThe combined organic extracts were washed (water, brine)
3. 3
   Dryingdried (Na2SO4)
4. 4
   Filtrationfiltered
5. 5
   Otherevaporated

Procedure

A mixture of ethyl p-hydroxybenzoate (4.98 g), benzyl bromoacetate (4.75 ml) and K2CO3 (4.14 g) was stirred for 15 hr in 30 ml of DMF. The reaction mixture was diluted with water (200 ml) and extracted with a 1:1 ether:hexane mixture. The combined organic extracts were washed (water, brine), dried (Na2SO4), filtered, and evaporated leaving 9.3 g, (99%) of the title compound as a heavy oil; TLC, Rf =0.71, Et2O: hexane (1:1).

Source