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

HRID 1673399
Notes
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Reaction equation

HRID 1673399 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 57879324Methyl 2-(benzamido)-4-(benzyloxy)benzoate

Product 1

HCID 578794652-(Benzamido)-4-(benzyloxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. customthe solvent was evaporated under reduced pressure and water and diethyl ether
  3. additionwere added
  4. customThe aqueous layer was separated
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes