Methanol → 2-(Benzamido)-4-(benzyloxy)benzoic acid

HRID 1673399Notes

Reaction equation

[OH-].[Na+].CO.[C:5]([NH:13][C:14]1[CH:23]=[C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:21]=[CH:20][C:15]=1[C:16]([O:18]C)=[O:17])(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>O1CCCC1>[C:5]([NH:13][C:14]1[CH:23]=[C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:21]=[CH:20][C:15]=1[C:16]([OH:18])=[O:17])(=[O:12])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 50 °C

Procedure

0.11 mL of 2.0 mol/L aqueous sodium hydroxide was added dropwise to a mixed solution of 1 mL of methanol and 2 mL of tetrahydrofuran containing 70 mg of methyl 2-(benzamido)-4-(benzyloxy)benzoate at room temperature, and stirred at the same temperature for 6 hours and 30 minutes, at 40° C. for 1 hour and 30 minutes and at 50° C. for 2 hours. After the reaction mixture was cooled to room temperature, the solvent was evaporated under reduced pressure and water and diethyl ether were added. The aqueous layer was separated and pH was adjusted to pH 4.0 with 1.0 mol/L hydrochloric acid. A solid substance was separated by filtration to obtain 35 mg of 2-(benzamido)-4-(benzyloxy)benzoic acid as white solid.

Workup

temperatureAfter the reaction mixture was cooled to room temperature
customthe solvent was evaporated under reduced pressure and water and diethyl ether
additionwere added
customThe aqueous layer was separated
customA solid substance was separated by filtration

Sources & evidence

ORD record: ord-8395518e9142413b9f25c7e505f049a1
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07999132B2

Reaction notes

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