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

HRID 1488907Notes

Reaction equation

HRID 1488907 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](Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+].Cl>CC(C)=O.O.C(O)C>[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

9

Reactant 5

HCID 1354-Hydroxybenzoic AcidHCID 313Hydrochloric AcidHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 14798Sodium Hydroxide

Product 1

HCID 738804-(Benzyloxy)benzoic acidYield 71.2%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A suspension of p-hydroxybenzoic acid (200 g, 1.2 mole), benzyl chloride (190 g, 1.5 mole) and potassium carbonate (165 g, 1.2 mole) in acetone (1200 ml) was reacted with stirring for 12 hours under reflux. After cooling, the precipitate was filtered off, and the filtrate was concentrated until 400 ml. H2O (1 l) was added with stirring to the residue and the mixture was allowed to stand. The organic layer separated was concentrated. The residue was added to a solution of NaOH (60 g, 1.5 mole) in H2O (1 l) and ethanol (500 ml), and stirred for 4 hours and dissolved. Then conc. hydrochloric acid (200 ml) was added to make pH 1. The precipitate was filtered, washed with H2O and with ethanol, and dried to give 195 g of 4-benzyloxybenzoic acid as white crystals having a m.p. of 191.2°-192.6° C.

Workup

  1. customwas reacted
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. filtrationthe precipitate was filtered off
  5. concentrationthe filtrate was concentrated until 400 ml
  6. additionH2O (1 l) was added
  7. stirringwith stirring to the residue
  8. customThe organic layer separated
  9. concentrationwas concentrated
  10. stirringstirred for 4 hours
  11. dissolutiondissolved
  12. filtrationThe precipitate was filtered
  13. washwashed with H2O and with ethanol
  14. customdried

Sources & evidence

ORD record
ord-089a7c7353854b54be4708eee13adab0
Source dataset
uspto-grants-1997_10
Patent number
US05677112

Reaction notes

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