Sulfuric Acid → Ethyl 3-hydroxyoctanoate

Participants

Reaction Conditions

Reaction Steps

7.64 g (0.117 mol) of zinc pretreated as described in Reference Example 1 were suspended in 50 ml of toluene, the mixture was heated to 83° C., the heat source was subsequently removed and a mixture of 11.4 ml (0.103 mol) of ethyl bromoacetate and 11.23 ml (0.0935 mol) of hexanal was added dropwise over a period of 30 minutes. After a brief induction phase, rigorous foaming and heating of the reaction mixture to 110° C. was observed. After all the mixture had been added, the resulting suspension was cooled to 8° C. by means of an ice/water mixture, after which 15 ml of 50% strength sulfuric acid was added dropwise at such a rate that the temperature of the suspension did not exceed 35° C. After phase separation, the organic phase was washed twice with 15 ml of water and dried over sodium sulfate. After filtration and removal of all volatile constituents on a rotary evaporator at 50° C./5 torr, the residue obtained was distilled in an oil pump vacuum at 2.5 torr. The fraction comprising ethyl 3-hydroxyoctanoate went over at 88-93° C. Yield: 12.25 g (70%).

Provenance & Evidence