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

HRID 1836972Notes

Reaction equation

HRID 1836972 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CO.[Cl-].C(C([NH3+])(C(=O)CCCCCCC)C(=O)CCCCCCC)(=O)CCCCCCC>[CH2:11]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 738804-(Benzyloxy)benzoic acidYield 55%

Reagents, catalysts & solvents 2

HCID 77620884Tricaprylylmethyl ammonium chlorideCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-hydroxybenzoic acid (5.52 g; 40 mole), benzyl bromide (11.89 mL; 0.1 mol) and tricaprylylmethylammonium chloride (100 mg, Aliquat 336® Henkel Corporation) in methanol (50 mL) was refluxed in presence of potassium carbonate (16.52 g) for 12 hours. The reaction mixture was then poured slowly into a solution of 2N hydrochloric acid solution. The precipitated acid was filtered, dried and recrystallized from hexane/ethyl acetate to give 5 g of 4-benzyloxybenzoic acid (yield=55%).

Workup

  1. filtrationThe precipitated acid was filtered
  2. customdried
  3. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-16fe2370be994f8b8225dac321b5b242
Source dataset
uspto-grants-2004_08
Patent number
US06780865B1

Reaction notes

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