Water → Propanoic acid, 3-(2-butoxyethoxy)-

Participants

Reaction Conditions

Reaction Steps

2 ml (3.2 mmol, 10 mol %) of a 1.6N solution of butyllithium in hexane are added dropwise, under N2, at 10° C. to a solution of 3.8 g (32 mmol) of 2-butoxyethanol in 2 ml of tetrahydrofuran. The solution is stirred for 5 minutes at 10° C. Then 2.5 ml (38 mmol) of acrylonitrile are added. The reaction mixture is heated to 55° C. and stirred for 2.5 hours at this temperature. Then a further 0.25 ml (3.8 mmol) of acrylonitrile is added and the mixture is stirred for another hour at 55° C. The reaction mixture is cooled to RT and afterwards poured into water. After acidification with 2N HCl (2 ml) and extraction with toluene, the organic phase is washed with an aqueous saturated solution of NaCl, dried over magnesium sulfate and concentrated on a vacuum rotary evaporator. The crude 3-(2-buthoxyethoxy)propionitrile (4.4 g) is taken up in 15 ml of concentrated hydrochloric acid and the solution is heated for 2.5 hours to 80° C. The resultant brown solution is cooled to RT, diluted with water and and extracted once more with ethyl acetate. The organic phases are combined, washed with an aqueous saturated solution of NaCl, dried over MgSO4, concentrated on a vacuum rotary evaporator and dried under a high vacuum, affording 3.2 g (53%) of 3-(2-butoxyethoxy)propionic acid as a pale brown liquid.

Provenance & Evidence