Benzyl Bromide → Benzyl 4-formylbenzoate

HRID 2184215Notes

Reaction equation

HRID 2184215 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O>[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:8])=[CH:5][CH:4]=1)=[O:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 120884-Formylbenzoic acid

Product 1

HCID 11528845Benzyl 4-formylbenzoateYield 104.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

304 g (2 mol) of 4-formylbenzoic acid were dissolved in 1 l of dimethylformamide (DMF), 304 g (2.2 mol) of potassium carbonate were added and then over a period of 30 min 261 ml (2.2 mol) of benzyl bromide were added at about 40° C. (exothermic reaction). The mixture was stirred for further 4 h at 40° C. to 45° C. Then the reaction mixture was poured into 3 l of ice-water and extracted for times with 1 l each of ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and the ethyl acetate removed in a rotary evaporator at reduced pressure. 503 g of an oil were obtained. The crude product was used directly in the next reaction step.

Workup

  1. custom(exothermic reaction)
  2. extractionextracted for times with 1 l each of ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. customthe ethyl acetate removed in a rotary evaporator at reduced pressure

Sources & evidence

ORD record
ord-0d029f992c6a4355b65aaaf21dae9706
Source dataset
uspto-grants-2005_05
Patent number
US06900318B1

Reaction notes

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