Methyl Ethyl Ketone → 2-Bromoethyl cinnamate

HRID 1745389Notes

Reaction equation

HRID 1745389 reaction equation
[C:1](Cl)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(C(C)=O)C.[Br:17][CH2:18][CH2:19][OH:20]>N1C=CC=CC=1>[C:1]([O:20][CH2:19][CH2:18][Br:17])(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6569Methyl Ethyl KetoneHCID 108982-BromoethanolHCID 660233-Phenylprop-2-enoyl chloride

Product 1

HCID 543970042-Bromoethyl cinnamateYield 94.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

83.3 g (0.5 mol) of cinnamic acid chloride and 200 mL of methyl ethyl ketone were placed in a reaction vessel. 62.5 g (0.5 mol) of 2-bromoethanol and 50 g of pyridine were added dropwise in the reaction vessel. The solution was refluxed with stirring for 2 hours under a nitrogen atmosphere and then concentrated. 100 mL of water was added to the concentrated solution. After extraction with chloroform, dehydration with anhydrous sodium sulfate, concentration, and drying, 121 g of 2-bromoethyl cinnamate was obtained.

Workup

  1. temperatureThe solution was refluxed
  2. concentrationconcentrated
  3. addition100 mL of water was added to the concentrated solution
  4. extractionAfter extraction with chloroform, dehydration
  5. concentrationwith anhydrous sodium sulfate, concentration
  6. customdrying

Sources & evidence

ORD record
ord-d1c01b38e0fa4cc8b88697ac755b52d9
Source dataset
uspto-grants-2006_03
Patent number
US07019104B1

Reaction notes

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