Benzyl Bromide → Benzyl crotonate, (E)-

HRID 445991Notes

Reaction equation

HRID 445991 reaction equation
[C:1]([OH:6])(=[O:5])/[CH:2]=[CH:3]/[CH3:4].C(=O)([O-])[O-].[K+].[K+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(OCC)(=O)C>CN(C)C=O>[C:1]([O:6][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:5])/[CH:2]=[CH:3]/[CH3:4]

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 637090Crotonic Acid

Product 1

HCID 5356259Benzyl crotonate, (E)-Yield 104.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Crotonic acid (70 g, 812 mmol) was dissolved in N,N-dimethylformamide (467 ml), which was cooled in an ice bath under nitrogen, and potassium carbonate (61.6 g, 447 mmol) was added. Benzyl bromide (91.7 ml, 772 mmol) was added dropwise to the reaction mixture over 20 minutes. The reaction mixture was stirred at mom temperature for 18 hours. Ethyl acetate was added to the reaction mixture, which was filtered through Celite. The filtered ethyl acetate solution was washed with water, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution. The organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound (142 g, yield: 99.4%).

Workup

  1. temperaturewhich was cooled in an ice bath under nitrogen
  2. filtrationwas filtered through Celite
  3. washThe filtered ethyl acetate solution was washed with water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9af4c0b65ca5456cb65d60920fccdfc3
Source dataset
uspto-grants-2013_07
Patent number
US08476301B2

Reaction notes

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