2-Bromoethanol → 2-Bromoethyl cinnamate

HRID 1745386Notes

Reaction equation

HRID 1745386 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.[Br:12][CH2:13][CH2:14][OH:15].Cl.N1C=CC=CC=1>C(C(C)=O)C>[C:1]([O:15][CH2:14][CH2:13][Br:12])(=[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 108982-BromoethanolHCID 660233-Phenylprop-2-enoyl chlorideHCID 10176127Pyridinium chloride

Product 1

HCID 543970042-Bromoethyl cinnamateYield 86.9%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

35.3 g (0.212 mol) of cinnamic acid chloride and 100 mL of methyl ethyl ketone were placed in a reaction vessel and stirred at room temperature under a nitrogen atmosphere. Then 28.2 g (0.225 mol) of 2-bromoethanol and 21 g of pylidine were dissolved in 100 mL of methyl ethyl ketone. The resulting solution was added dropwise in the aforementioned reaction vessel at room temperature, and then refluxed with stirring for 2 hours. After cooling the solution, pyridine hydrochloride was precipitated and then separated from the solution by filtration. The filtrate was concentrated and then dissolved in methylene chloride. The solution of methylene chloride was poured into a separating funnel and washed with water. Then the solution was dried with sodium sulfuric anhydride and concentrated. Thus 47 g (86.9% yield) of 2-bromoethyl cinnamate was obtained.

Workup

  1. additionThe resulting solution was added dropwise in the aforementioned reaction vessel at room temperature
  2. temperaturerefluxed
  3. stirringwith stirring for 2 hours
  4. customwas precipitated
  5. customseparated from the solution by filtration
  6. concentrationThe filtrate was concentrated
  7. dissolutiondissolved in methylene chloride
  8. additionThe solution of methylene chloride was poured into a separating funnel
  9. washwashed with water
  10. dry with materialThen the solution was dried with sodium sulfuric anhydride
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-be58923d696248ccaa64903e97082b60
Source dataset
uspto-grants-2006_03
Patent number
US07019104B1

Reaction notes

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