Hydrochloric Acid → 4-(Benzyloxy)benzoic acid

HRID 1840940Notes

Reaction equation

HRID 1840940 reaction equation
[Li+].[OH-].C[O:4][C:5](=[O:20])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][CH:7]=1.Cl>C1COCC1>[CH2:13]([O:12][C:9]1[CH:8]=[CH:7][C:6]([C:5]([OH:20])=[O:4])=[CH:11][CH:10]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 299810Methyl 4-(benzyloxy)benzoate

Product 1

HCID 738804-(Benzyloxy)benzoic acidYield 98.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

16 mL of a 2N LiOH aqueous solution were added to a solution of 3.0 g (12.5 mmol) of 4-benzyloxy-benzoic acid methyl ester in 50 mL of THF and the mixture was refluxed overnight. The reaction mixture was acidified with HCl 6N and extracted with ethyl acetate affording after filtration and removal of the solvent under reduced atmosphere, 2.8 g (93% yield) of 4-benzyloxy-benzoic acid.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. extractionextracted with ethyl acetate affording

Sources & evidence

ORD record
ord-19a0358be6034e059228d05e1569e5c6
Source dataset
uspto-grants-2004_01
Patent number
US06683096B2

Reaction notes

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