Ethylene Glycol → HCID 14119832, compound

Participants

Reaction Conditions

Reaction Steps

To 56.1 g of potassium t-butoxide, 150 ml of ethylene glycol was dropwise added in a stream of nitrogen to dissolve potassium t-butoxide completely. To the solution, 45.3 g of 1-bromobenzocyclobutene (synthesized according to a method of DeCamp et al., J. Org. Chem., 1981, 46, 3918) was dropwise added. After the addition was completed, the mixture was heated to 80° C., and stirred for 8 hours. The mixture was cooled to room temperature, and poured into ice-cold water. After adjusting pH to 6 with hydrochloric acid, an organic phase was extracted with ethyl acetate. After the solvent was distilled away, the residue was purified in a silica gel chromatography to obtain 20.6 g of 1-(2′-hydroxyethoxy)-benzocyclobutene.

Provenance & Evidence