Hydrochloric Acid → Ethyl (2-hydroxy-2,3-dihydro-1H-inden-2-yl)acetate

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-indanone (13.2 g), ethyl bromoacetate (16.7 g), benzene (150 ml) and purified zinc (6.5 g) is stirred and heated at 50° C. Iodine (0.5 g) is added to catalyze the reaction. A rather vigorous reaction sets in after about 30 min. and the heating is discontinued. After the mixture ceases boiling, 4 g of fresh zinc and 10 g of ethyl bromoacetate is added, the reaction mixture is heated at reflux for 2 hr. and allowed to stand overnight at room temperature. The zinc addition-compound is decomposed by adding 200 ml of cold 10% hydrochloric acid. The aqueous layer is separated, extracted twice with benzene, all organic extracts are combined and dried (MgSO4). The filtrate is concentrated and the residue distilled under reduced pressure yielding 2-hydroxyindane-2-acetic acid ethyl ester, bp. 163°-166° C/10 mm.

Provenance & Evidence