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

HRID 866373Notes

Reaction equation

HRID 866373 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+].[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[C:6]([C:5]1[CH:9]=[CH:10][C:2]([O:1][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:3][CH:4]=1)([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 7503Benzyl ChlorideHCID 14798Sodium Hydroxide2×

Product 1

HCID 738804-(Benzyloxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

138 g. (1 mole) of 4-hydroxybenzoic acid was dissolved in 1 liter of 95% ethanol and 500 ml. of 2N sodium hydroxide solution. To this solution was added 346 ml. (3 mole) of benzyl chloride and the mixture was boiled under reflux. 1 liter of 5N sodium hydroxide was added dropwise over a period of 2 hours and the mixture heated a further hour with stirring. The solvent was distilled to half its volume, 2 liters of water added, the warm aqueous solution acidified with hydrochloric acid and the precipitated product recrystallised from 80% ethanol, m.p. 188° C.

Workup

  1. additionTo this solution was added 346 ml
  2. temperatureunder reflux
  3. temperaturethe mixture heated a further hour
  4. distillationThe solvent was distilled to half its volume, 2 liters of water
  5. additionadded
  6. customthe precipitated product recrystallised from 80% ethanol, m.p. 188° C.

Sources & evidence

ORD record
ord-74f2b016c28d420bb72e8e1e3251cd37
Source dataset
uspto-grants-1978_07
Patent number
US04098816

Reaction notes

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