Benzyl Bromide → HCID 86672797, compound

HRID 1755116Notes

Reaction equation

HRID 1755116 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:9]([C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][C:12]=1[OH:20])=[O:10].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([O:16][C:15](=[O:17])[C:14]1[CH:18]=[CH:19][C:11]([CH:9]=[O:10])=[C:12]([O:20][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 3175084-Formyl-3-hydroxybenzoic acid

Product 1

HCID 86672797HCID 86672797, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Benzyl bromide (2.17 ml, 18.3 mmol) was added to a solution of 4-formyl-3-hydroxy-benzoic acid (1.01 g, 6.10 mmol) and potassium carbonate (3.37 g, 24.4 mmol) in DMF (10 ml), and the mixture was stirred at 50° C. for five hours. The reaction solution was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 3-benzyloxy-4-formyl-benzoic acid benzyl ester (2.01 g, 95%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-1a29fbd01b384c6ebb80edbc87a9bdc7
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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