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Benzyl Bromide → Methyl 4-(2-benzyloxybenzyl)benzoate

HRID 1247715
Notes
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Reaction equation

HRID 1247715 reaction equation
[OH:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C)C=O>[CH2:25]([O:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 21909287Methyl 4-(2-hydroxybenzyl)benzoate

Product 1

HCID 21909320Methyl 4-(2-benzyloxybenzyl)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of methyl 4-(2-hydroxybenzyl)benzoate (1.5 g) and potassium carbonate (0.94 g) in N,N-dimethylformamide (200 mL) was added benzylbromide (0.81 mL), and the mixture was stirred at 50° C. for 5 hours. An insoluble material was removed by filtration, water and dilute hydrochloric acid was added to the filtrate, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=4/1) to give methyl 4-(2-benzyloxybenzyl)benzoate (2.1 g).

Workup

  1. customAn insoluble material was removed by filtration, water and dilute hydrochloric acid
  2. additionwas added to the filtrate
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-198e722f2e9f45669bd06094b6f1b506
Source dataset
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07129381B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes