Hydrochloric Acid → 3-{[3-Phenyl-3-(pyridin-3-yl)prop-2-en-1-yl]oxy}benzoic acid

HRID 4518Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:8][CH2:9][O:10][C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=2)[C:14]([O:16]C)=[O:15])[CH:2]=1.[OH-].[Na+].Cl>O.CO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:8][CH2:9][O:10][C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=2)[C:14]([OH:16])=[O:15])[CH:2]=1

Participants

Conditions

Temperature: 60 °C

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.

Workup

waitwhich was then left standing
temperaturefor cooling
extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with saturated saline
customdried
customthe solvent was evaporated off

Sources & evidence

ORD record: ord-b8e8a0e44dc8447099988bc5cd8e65ec
Source dataset: uspto-grants-1988_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04727078

Reaction notes

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