Ethanol → Ethyl 3-(3-bromophenyl)acrylate

HRID 372480Notes

Reaction equation

HRID 372480 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)/[CH:5]=[CH:6]/[C:7]([OH:9])=[O:8].S(=O)(=O)(O)O.[CH2:18](O)[CH3:19]>>[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)/[CH:5]=[CH:6]/[C:7]([O:9][CH2:18][CH3:19])=[O:8]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 776461m-Bromocinnamic acid

Product 1

HCID 5369361Ethyl 3-(3-bromophenyl)acrylate

Procedure

Trans m-bromocinnamic acid (14.8 g), ethanol (173 ml) and concentrated sulfuric acid (0.4 ml) were combined and heated at reflux for 15 hours. About 150 ml of the ethanol was distilled off, and the remaining solution was poured into ice/water (140 ml). The cold mixture was made strongly alkaline with 40% sodium hydroxide and extracted with methylene chloride (4 × 60 ml). The combined methylene chloride extract was dried over anhydrous potassium carbonate. The potassium carbonate was removed by filtration and the solvent stripped off under reduced pressure. Trans ethyl 3-bromocinnamate, was obtained as a partially solidified oil. (IR spectrum was consistent with this compound).

Workup

  1. temperatureheated
  2. temperatureat reflux for 15 hours
  3. distillationAbout 150 ml of the ethanol was distilled off
  4. additionthe remaining solution was poured into ice/water (140 ml)
  5. extractionextracted with methylene chloride (4 × 60 ml)
  6. extractionThe combined methylene chloride extract
  7. dry with materialwas dried over anhydrous potassium carbonate
  8. customThe potassium carbonate was removed by filtration

Sources & evidence

ORD record
ord-9870d426fd5b4195b7ebc741da7d9143
Source dataset
uspto-grants-1978_05
Patent number
US04091112

Reaction notes

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