Water → (4-Chloro-phenyl)-prop-2-ynyloxy-acetic acid

Participants

Reaction Conditions

Reaction Steps

4-Chloro-benzaldehyde (7.2 g) in propargyl alcohol (15 ml) is heated to 50° C. A mixture of potassium hydroxide (31.2 g, assay 90%) in propargyl alcohol (150 ml) as well as a mixture of bromoform (13 g) in propargylalcohol (15 ml) are added simultaneously over 1 hour at 50° C. The reaction mixture is stirred at 50° C. for additional 5 hours. After cooling to room temperature water (150 ml) is added. The resulting mixture is extracted with tert butyl methyl ether (150 ml). The organic phase is again extracted with 4M potassium hydroxide (50 ml). The aqueous alkaline extracts are combined and made acidic (pH<3) by addition of concentrated hydrochloric acid. The aqueous phase is extracted with tert butyl methyl ether (2×150 ml). The organic phases are combined, extracted with water (1×100 ml), dried (magnesium sulfate) and evaporated. (4-Chloro-phenyl)-prop-2-ynyloxy-acetic acid (10.4 g) is obtained as oil, which solidifies on standing.

Provenance & Evidence