Hydrochloric Acid → Benzyl 4-benzyloxy-2-chlorobenzoate

HRID 1828802Notes

Reaction equation

HRID 1828802 reaction equation
Cl[C:2]1[CH:10]=[C:9](O)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[C:12](=[O:15])([O-])[O-:13].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[ClH:26]>CN(C)C=O>[CH2:4]([O:6][C:2]1[CH:10]=[CH:9][C:8]([C:12]([O:13][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:15])=[C:7]([Cl:26])[CH:3]=1)[C:3]1[CH:2]=[CH:10][CH:9]=[CH:8][CH:7]=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

To a solution of 2-chloro-4-hydroxybenzoic acid (695 mg) in N,N-dimethylformamide (3.5 ml) were added potassium carbonate (1.67 g) and benzyl bromide (1.73 g) and the mixture was stirred at room temperature for 14 hr. To the reaction mixture was added 1N hydrochloric acid and the resulting product was extracted 3 times with diethyl ether. The organic layers were combined and washed successively with water, saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was recrystallized from diisopropyl ether/hexane to give benzyl 4-benzyloxy-2-chlorobenzoate (1.13 g) as a pale-yellow powder.

Workup

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

Sources & evidence

ORD record
ord-e5c66dd5d96f4cc0b34fd059d4ff85d3
Source dataset
uspto-grants-2006_06
Patent number
US07060721B1

Reaction notes

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