Hydrochloric Acid → Benzyl 4-benzyloxy-2-chlorobenzoate

HRID 1699912Notes

Reaction equation

HRID 1699912 reaction equation
[C:1](=[O:4])([O-])[O-:2].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl[C:16]1[CH:24]=[C:23](O)[CH:22]=[CH:21][C:17]=1[C:18]([OH:20])=O.[ClH:26]>CN(C)C=O>[CH2:18]([O:20][C:8]1[CH:13]=[CH:12][C:11]([C:1]([O:2][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:4])=[C:10]([Cl:26])[CH:9]=1)[C:17]1[CH:16]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 918212-Chloro-4-hydroxybenzoic acid

Product 1

HCID 22058608Benzyl 4-benzyloxy-2-chlorobenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (1.67 g) and benzyl bromide (1.73 g) were added to a solution of 2-chloro-4-hydroxybenzoic acid (695 mg) in N,N-dimethylformamide (3.5 ml) and the mixture was stirred for 14 hr at room temperature. To the reaction mixture was added 1N hydrochloric acid and the resulting product was extracted three times with ether. The organic layers were combined, washed successively with water, a saturated aqueous solution of sodium hydrogencarbonate and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was recrystallized from diisopropyl ether/hexane to give the objective compound (1.13 g) as a pale-yellow powder.

Workup

  1. extractionthe resulting product was extracted three times with ether
  2. washwashed successively with water
  3. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and saturated brine, and dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was recrystallized from diisopropyl ether/hexane

Sources & evidence

ORD record
ord-449931831d644c39831f339223dbb3da
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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