Sodium Hydroxide → 4-(Benzyloxy)benzoic acid

HRID 889006Notes

Reaction equation

HRID 889006 reaction equation
C[O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1.[OH-].[Na+]>C1COCC1.CO.O>[CH2:11]([O:10][C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:18])=[O:2])=[CH:9][CH:8]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 299810Methyl 4-(benzyloxy)benzoate

Product 1

HCID 738804-(Benzyloxy)benzoic acidYield 92.9%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
52.5 °C

Procedure

4-Benzyloxy-benzoic acid methyl ester (8.0 g, 0.033 mol) was dissolved in THF:methanol:water (3:2:1, 80 ml) and NaOH (1.98 g, 0.05 mol) was added to the reaction mixture and stirred at 50-55° C. for 3 hours. Solvents were removed and residue was diluted with water, washed with hexane and acidified with dil HCl to obtain 4-benzyloxy-benzoic acid (7.0 g, 92%) as a white solid.

Workup

  1. customSolvents were removed
  2. additionresidue was diluted with water
  3. washwashed with hexane

Sources & evidence

ORD record
ord-cc9cd98ee00841cf96228c672b11787d
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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