Hydrochloric Acid → Methyl 4-(benzyloxy)-2-hydroxybenzoate

HRID 1377725Notes

Reaction equation

HRID 1377725 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl>CC(C)=O>[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 16523Methyl 2,4-Dihydroxybenzoate

Product 1

HCID 225489Methyl 4-(benzyloxy)-2-hydroxybenzoateYield 60%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of methyl 2,4-dihydroxybenzoate (50 gm, 300 mmol) in acetone (1 L) was added potassium carbonate (150 gm) and benzyl bromide (37 mL, 1.1 eq). The mixture was refluxed for 6 hours and cooled to ambient temperature. The reaction was poured into ice cold aqueous 1M HCl (1 L) and the aqueous mixture was extracted with ether (3×500 mL). The combined organic extracts were dried over MgSO4 and filtered and the solvent was removed under reduced pressure. Methyl 2-hydroxy-4-benzyloxybenzoate was obtained by crystallization from EtOH in 60% yield.

Workup

  1. temperatureThe mixture was refluxed for 6 hours
  2. extractionthe aqueous mixture was extracted with ether (3×500 mL)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ab9cf93f59304237917d06b900d6bd9e
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Reaction notes

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