反应详情

{2-Chloro-3-[(diphenylcarbamoyloxy)methyl]phenoxy}acetic acid methyl ester (0.64 g, 1.5 mmol) was dissolved in a mixture of methanol (20 mL), water (5 mL), and tetrahydrofuran (2 mL). An aqueous solution of lithium hydroxide (0.07 g, 1.65 mmol) was added and the mixture was allowed to stir overnight. The mixture was concentrated in vacuo, and the residue diluted with water and washed with diethyl ether. The aqueous layer was acidified with 3M hydrochloric acid forming a white precipitate which was filtered and dried. Recrystallization from methanol gave {2-chloro-3-[(diphenylcarbamoyloxy)methyl]phenoxy}acetic acid as white needles (0.47 g, 76.5%); m.p. 182.2-182.9° C.; 1H NMR 4.66 (s, 2H), 5.30 (s, 2H), 6.83 (dt, J=7.5Hz, 2H), 7.11 (t, J=8.0Hz), 7.28 (m, 10H); 13C NMR 64.98 (t), 66.02 (t), 112.96 (d), 121.62 (d), 126.27 (d), 126.93 (d), 127.02 (d), 128.94 (d), 135.79 (s), 142.34 (s), 153.68 (s), 154.27 (s), 170.26 (s). Analysis for C22H18ClNO5: Calcd.: C, 64.16; H, 4.41; N, 3.40. Found: C, 64.30; H, 4.39; N, 3.56.

1. concentrationThe mixture was concentrated in vacuo
2. additionthe residue diluted with water
3. washwashed with diethyl ether
4. filtrationwas filtered
5. customdried
6. customRecrystallization from methanol