Hydrochloric Acid → 3-(Benzyloxy)benzoic acid

HRID 380126

Reaction equation

HRID 380126 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=1)[C:12]([O:14]C)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>COCCOC>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=1)[C:12]([OH:14])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13368031Methyl 3-(benzyloxy)benzoate

Product 1

HCID 3092263-(Benzyloxy)benzoic acidYield 97.7%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of methyl 3-benzyloxybenzoate (38.0 g) and 5N NaOH solution (207 ml) in 1,2-dimethoxyethane (207 ml) was stirred at room temperature for 3 hours 30 minutes and at 100° C. for 1 hour 20 minutes. The reaction mixture was cooled with ice water, mixed with 6N HCl (1.1 mole), and extracted with diethyl ether. The extract was washed with brine, dried over MgSO4, and evaporated in vacuo to afford 3-benzyloxybenzoic acid (34.96 g) as a colorless powder.

Workup

  1. extractionextracted with diethyl ether
  2. washThe extract was washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-d8ec4d9da1df4d6e84697fca93065a3d
Source dataset
uspto-grants-2001_10
Patent number
US06300344B1

Linked notes

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