Reaction #4614

Reaction equation

Methyl 3-[3-(3-pyridyl)-3-phenyl-2-propenyloxy]benzoate

sodium hydroxide

hydrochloric acid

→

3-[3-(3-pyridyl)-3-phenyl-2-propenyloxy]benzoic acid

Yield 80.0%

Solvents

water

water

methanol

Conditions

Workup

1. 1
   workup.WAITwhich was then left standing
2. 2
   Temperaturefor cooling
3. 3
   Extractionfollowed by extraction with ethyl acetate
4. 4
   WashThe organic layer was washed with saturated saline
5. 5
   Otherdried
6. 6
   Otherthe solvent was evaporated off

Procedure

Methyl 3-[3-(3-pyridyl)-3-phenyl-2-propenyloxy]benzoate (If-56, 1.5 g, 4.35 mmoles) was dissolved in a mixture of water (3 ml) and methanol (10 ml). To the solution was added sodium hydroxide (700 mg, 17.5 mmoles). The mixture was stirred for 2 hours at 60° C., which was then left standing for cooling. To the reaction solution was added water, the pH of which was adjusted to 5 with 1N hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline, dried and the solvent was evaporated off. The residue was subjected to silica-gel column chromatography using ethyl acetate as eluant to yield 3-[3-(3-pyridyl)-3-phenyl-2-propenyloxy]benzoic acid (Ie-46) (1.15 g, 80%). Hydrolysis analogous to the above afforded substituted vinyl carboxylic acid derivatives (Ie-45-Ie-51, Ie-53, Ie-54) shown in Table 4-1.

Source