4-Hydroxybenzoic Acid → 4-(Benzyloxy)benzoic acid

HRID 1178061Notes

Reaction equation

HRID 1178061 reaction equation
[OH-].[K+].[CH2:3](Br)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=1.Cl>CCO.O.O>[CH2:3]([O:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 14797Potassium Hydroxide2×

Product 1

HCID 738804-(Benzyloxy)benzoic acidYield 62.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 19096565Water ethanolSolvent

Procedure

KOH (6.16 g, 109.78 mmol) and benzyl bromide (9.42 g, 55.08 mmol) were added to a stirred solution of 4-hydroxy benzoic acid (6.9 g, 49.96 mmol) in EtOH:H2O (9:1, 176 mL) and the resulting mixture was heated to reflux for 20 hrs. 20% KOH solution (60 mL) was then added the mixture maintained at reflux for 4 hours. The reaction mixture was diluted with water (200 mL) and acidified with 20% HCl. The resulting white precipitate was filtered and washed with water followed by hexane to afford 7.1 g (62.2% yield) of 4-benzyloxy benzoic acid. 1H NMR (DMSO-d6): δ 12.6 (s, 1H), 7.9 (d, 2H), 7.4 (m, 5H), 7.1 (d, 2H), 5.2 (s, 2H).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 20 hrs
  3. temperaturemaintained
  4. temperatureat reflux for 4 hours
  5. filtrationThe resulting white precipitate was filtered
  6. washwashed with water

Sources & evidence

ORD record
ord-ec107cb9b6e5424f80b626237dc75239
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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