Acetic Acid → 3-(2,3-dihydro-1,4-benzodioxin-2-yl)propanoic acid

Reaction equation

C(C[CH2:4][CH:5]1[O:10][C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[O:7][CH2:6]1)#N.S(=O)(=O)(O)O.[C:20]([OH:23])(=[O:22])[CH3:21]>O>[O:10]1[C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[O:7][CH2:6][CH:5]1[CH2:4][CH2:21][C:20]([OH:23])=[O:22]

Participants

Procedure

72 g 2-(2-cyanoethyl) (2,3-dihydro [4H] 1,4-benzodioxin) are suspended in 100 ml acetic acid, 100 ml water and 40 g sulphuric acid. The whole is heated to reflux for 48 hours and the mixture is thereafter poured in water. The aqueous phase is extracted with ether. The ethereous solution is separated, washed, dried and concentrated off. 76 g of 3-(2,3-dihydro [4H] 1,4-benzodioxin-2 yl) propionic acid are obtained, melting at 102°. This acid is esterified with methanol and p toluene sulphonic acid at the boiling point for 18 hours. After the usual purifications 71 g of the methyl ester are obtained. MP: 55°.