Hydrochloric Acid → 3-Benzyloxy-4-hydroxyphenylacetic acid

Reaction equation

C([O:3][C:4](=[O:21])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:7]=1)C.[OH-].[Na+].Cl>O>[CH2:14]([O:13][C:8]1[CH:7]=[C:6]([CH2:5][C:4]([OH:21])=[O:3])[CH:11]=[CH:10][C:9]=1[OH:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Procedure

5.35 g of the ester obtained above was added to a mixture of 50 ml of water and 1.49 g of sodium hydroxide. The resultant solution was refluxed for 2.5 hours, acidified with concentrated hydrochloric acid and evaporated under reduced pressure to give solids, which were purified by Soxhlet extraction apparatus to provide 4.27 g(yield 89%) of the desired compound as a yellow solid, having the characteristics of: m.p. 130°-133° C.; NMR(CDCl3, 200 MHz) δ3.45(s, 2H, CH2Ar), 5.09 (s, 2H, OCH2), 6.75-7.40(m, 6H, ArH).