Acetic Acid → 2,3-Dihydro-5-benzofuranacetic acid

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][C:8](CC(N3CCOCC3)=S)=[CH:9][C:4]=2[CH2:3][CH2:2]1.[C:19]([OH:22])(=[O:21])[CH3:20].S(=O)(=O)(O)O>O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:20][C:19]([OH:22])=[O:21])=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

Procedure

2,3-dihydrobenzofuran-5-ylthioacetic acid morpholide (5.0 g) was heated at reflux in a solution of acetic acid (20 ml), concentrated sulfuric acid (3.0 ml) and water (4.5 ml). After 3 hours the reaction mixture was cooled and added to water. The product was extracted with ethyl acetate and the combined extracts washed five times with water. The organic solution was then extracted with aqueous saturated sodium bicarbonate solution. The aqueous solution was then acidified and extracted with ethyl acetate. The combined extracts were dried over sodium sulfate and evaporated to give a residue which was recrystallized from acetone/hexane to give 2,3-dihydrobenzofuran-5-ylacetic acid, m.p. --96°-98° C.