Hydrochloric Acid → 4-methoxy-3-[(E)-2-(4-trifluoromethoxyphenyl)vinyl]benzoic acid

HRID 558388Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9]CC)=[O:8])=[CH:5][C:4]=1/[CH:14]=[CH:15]/[C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=1.[OH-].[K+].Cl>CO>[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1/[CH:14]=[CH:15]/[C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]([F:24])([F:25])[F:26])=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Ethyl 4-methoxy-3-[(E)-2-(4-trifluoromethoxyphenyl)vinyl]benzoate (4.5 g) obtained in step A was dissolved in 40 mL of methanol, and 16 mL of a 20% aqueous solution of potassium hydroxide was added. The resulting solution was stirred for 2 hours at 80° C., and then cooled to room temperature. The reaction mixture was adjusted to pH of about 3 with the use of 60 mL of 1 M hydrochloric acid. The resulting precipitate was separated by filtration, washed with water, and then dried over diphosphorus pentoxide under reduced pressure to obtain 4.1 g (99%) of 4-methoxy-3-[(E)-2-(4-trifluoromethoxyphenyl)vinyl]benzoic acid.

Workup

temperaturecooled to room temperature
customThe resulting precipitate was separated by filtration
washwashed with water
dry with materialdried over diphosphorus pentoxide under reduced pressure

Sources & evidence

ORD record: ord-3dd7289d21734674bd5947be250718fb
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063046B2

Reaction notes

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