Reaction #1862

Reaction equation

ethyl 2-oxobicyclo[3.1.0]hexane-6-carboxylate

hydrochloric acid

→

title compound

2-Oxobicyclo[3.1.0]hexane-6-carboxylic acid

Solvents

sodium hydroxide

Conditions

Workup

1. 1
   ExtractionThe resulting solution was extracted with ethyl acetate
2. 2
   DryingThe extracts were dried over magnesium sulfate
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated
5. 5
   Otherto give 49.1 g (98%) of the crude material
6. 6
   OtherRecrystallization from 100 ml of ethyl acetate

Procedure

A mixture of 60 g of ethyl 2-oxobicyclo[3.1.0]hexane-6-carboxylate and 300 ml of 1N sodium hydroxide was stirred at 25°-30° C. After 2.5 hours, concentrated hydrochloric acid was added to adjust the pH to 0.8-1.2. The resulting solution was extracted with ethyl acetate. The extracts were dried over magnesium sulfate, filtered, and concentrated to give 49.1 g (98%) of the crude material. Recrystallization from 100 ml of ethyl acetate gave the title compound, mp 123.5°-128° C.

Source