Hydrochloric Acid → 4-(Benzyloxy)benzoic acid

HRID 467238

Reaction equation

HRID 467238 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([OH:15])=[O:14])=[CH:17][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 299810Methyl 4-(benzyloxy)benzoate

Product 1

HCID 738804-(Benzyloxy)benzoic acidYield 96.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 15.0 g of methyl 4-benzyloxybenzoate in 225 ml of methanol were added 18.6 ml of a 5N solution of sodium hydroxide. The mixture was heated at reflux for 18 hours. The solution was cooled to room temperature and acidified to pH 3 by addition of 6N hydrochloric acid. The resulting white precipitate was filtered to give 13.6 g of the title compound: 300-MHz 1H NMR (DMSO-d6) δ5.18 (s, 2 H), 7.04 (d, J=9 Hz, 2 H), 7.26-7.49 (m, 5 H), 7.86 (d, J=9 Hz, 2 H), 12.3 (b s, 1 H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 hours
  3. filtrationThe resulting white precipitate was filtered

Sources & evidence

ORD record
ord-6987cc4982f64057b20ac5716afa3670
Source dataset
uspto-grants-1992_10
Patent number
US05159079

Linked notes

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