Glutaric anhydride → 5-Oxo-5-(2-thienyl)valeric acid

Participants

Reaction Conditions

Reaction Steps

Thiophene (19.5 ml) and glutaric anhydride (27.5 g) were mixed and heated to 60° C. under a nitrogen atmosphere until all solid dissolved. The heat was removed and 2.4 grams of 85% orthophosphoric acid was added. The reaction mixture was then heated to 100° C. for four hours, cooled, and 46 ml of water added. The mixture was extracted with ether then the ether phase was extracted with aqueous sodium hydroxide solution (2.5N). The aqueous phase was cooled and made acidic by addition of 6N hydrochloric acid. Solid which precipitated out was collected on a filter, washed with water and dried under vacuum at 60° C. Yield 9.2 g N.M.R. (CDCl3)δ2.1 (m, 2H), 2.54 (t, 2H), 3.04 (t, 2H), 7.14 (t, 1H), 7.64 (dd, 1H), 7.74 (d, 1H).

Provenance & Evidence