Methanol → 3-(Benzyloxy)benzoic acid

HRID 2361854Notes

Reaction equation

HRID 2361854 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-].[K+].CO>O>[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 887MethanolHCID 14797Potassium HydroxideHCID 13368031Methyl 3-(benzyloxy)benzoate

Product 1

HCID 3092263-(Benzyloxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 3-benzyloxybenzoate (23.9 g; 0.099 mol), potassium hydroxide (8.42 g; 0.15 mol) and methanol (100 cm3) was stirred at room temperature until a small sample in water gave a clear solution (−18 hrs). The solution was then evaporated to dryness and the colourless solid residue dissolved in water (100 cm3) and the resulting stirred solution was acidified slowly with 50% sulphuric acid (30 cm3). After stirring for ˜30 minutes, the crystalline precipitate was filtered, washed with water and dried in vacuo at 40° to give the title compound as a colourless powder.

Workup

  1. customgave a clear solution (−18 hrs)
  2. customThe solution was then evaporated to dryness
  3. dissolutionthe colourless solid residue dissolved in water (100 cm3)
  4. stirringAfter stirring for ˜30 minutes
  5. filtrationthe crystalline precipitate was filtered
  6. washwashed with water
  7. customdried in vacuo at 40°

Sources & evidence

ORD record
ord-3895de4b24ef40a78db8e79826241ae1
Source dataset
uspto-grants-2014_04
Patent number
US08691818B2

Reaction notes

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