Hydrochloric Acid → Ethyl alpha-oxobenzenebutanoate

Participants

Reaction Conditions

Reaction Steps

A 200 ml flask was charged with a solution dissolving 20.8 g (100 mmol) of 2-hydroxy-4-phenylbutyric acid ethyl ester in methylene chloride (50 ml) and 72.6 g (purity 12.3%, 120 mmol) of sodium hypochlorite, and cooled at 6° C. To the reaction mixture was added 43 mg (0.2 mmol) of 4-acetoxy-2,2,6,6-tetramethylpiperidinyl-1-oxy and further added 10 ml (10 mmol) of 1N hydrochloric acid. The gradual exothermal reaction proceeded, and the starting material of 2-hydroxy-4-phenylbutyric acid ethyl ester was disappeared in 30 minutes. After the reaction was stopped by adding 10 ml of 5% sodium thiosulfate aqueous solution, the reaction mixture was subjected to the after treatment as described in Example 1 to obtain 18.55 g of 2-keto-4-phenylbutyric acid ethyl ester. The yield was 90%.

Provenance & Evidence