Benzyl Bromide → HCID 21840988, compound

HRID 1739489Notes

Reaction equation

HRID 1739489 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[OH:13])[C:6]([O:8][CH3:9])=[O:7])=[O:2].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:6]([O:8][CH3:9])=[O:7])=[O:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 212595Benzoic acid, 3-formyl-4-hydroxy-, methyl ester

Product 1

HCID 21840988HCID 21840988, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 3-formyl-4-hydroxybenzoate (3.55 g, 19.7 mmol) in DMF (20 ml) was added benzyl bromide (3.70 g, 21.67 mmol) and K2CO3 (4.1 g, 29.6 mmol). The reaction was stirred at ambient temperature overnight and the solvent evaporated to dryness (at reduced pressure). The residue was partitioned between ethyl ether and water and the aqueous layer extracted a second time with ethyl ether. The organic extracts were combined, washed with brine, dried (MgSO4 ) and evaporated to give methyl 3-formyl-4-benzyloxybenzoate as an off-white solid which was used without further purification.

Workup

  1. customthe solvent evaporated to dryness (at reduced pressure)
  2. customThe residue was partitioned between ethyl ether and water
  3. extractionthe aqueous layer extracted a second time with ethyl ether
  4. washwashed with brine
  5. dry with materialdried (MgSO4 )
  6. customevaporated

Sources & evidence

ORD record
ord-bf0a1f1b36aa41c78ae7b910ee4508bb
Source dataset
uspto-grants-1999_10
Patent number
US05965741

Reaction notes

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