反应详情

Crude 2-[(E)-2-(3-chlorophenyl)vinyl]-5-methoxybenzoic acid methyl ester was suspended in methanol:THF:water (3:1:1 [v/v], 400 mL) and lithium hydroxide (12.10 g, 289 mmol) added. The mixture was stirred for 22 h at ambient temperature and concentrated in vacuo to give a pale brown solid. The crude product was re-dissolved in water (400 mL), the solution washed with diethyl ether (3×250 mL) and acidified to pH 2 with 1 N HCl (aq.). The aqueous was extracted with ethyl acetate (3×200 mL), the organic phase dried (MgSO4) and concentrated in vacuo to give a tan solid which was triturated with methanol and filtered to give (E)-2-[2-(3-chlorophenyl)vinyl]-5-methoxybenzoic acid (15.43 g, 53.44 mmol, 74% for 2 steps from 2-bromo-5-methoxybenzoic acid methyl ester) as an off-white powder.

1. concentrationconcentrated in vacuo
2. customto give a pale brown solid
3. washthe solution washed with diethyl ether (3×250 mL)
4. extractionThe aqueous was extracted with ethyl acetate (3×200 mL)
5. dry with materialthe organic phase dried (MgSO4)
6. concentrationconcentrated in vacuo
7. customto give a tan solid which
8. customwas triturated with methanol
9. filtrationfiltered