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Hydrochloric Acid → 5-(Benzyloxy)-2-methoxybenzoic Acid

HRID 1644582
Notes
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Reaction equation

HRID 1644582 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:19][CH3:20])=[C:13]([CH:18]=1)[C:14]([O:16]C)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C1COCC1.CO.[OH-].[Na+]>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:19][CH3:20])=[C:13]([CH:18]=1)[C:14]([OH:16])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 66775910Methyl 5-(benzyloxy)-2-methoxybenzoate

Product 1

HCID 132820475-(Benzyloxy)-2-methoxybenzoic AcidYield 88%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent
HCID 14798
Sodium Hydroxide
Solvent

Procedure

Methyl 5-benzyloxy-2-methoxybenzoate (3.72 g) was dissolved in a mixed solvent of THF (30 ml) and methanol (30 ml), and 1N aqueous sodium hydroxide solution (27.3 ml) was added to the mixed solution. The mixture was stirred at room temperature for 2 days, and 1N aqueous hydrochloric acid solution (40 ml) was added. The precipitate was collected by filtration and washed with water to give 5-benzyloxy-2-methoxybenzoic acid (3.10 g, 88%) as colorless crystals.

Workup

  1. additionwas added to the mixed solution
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-85415fe2cee244e1a4d931ead1f8405b
Source dataset
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08124617B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes