Ethanol → Ethyl 3-(3-bromophenyl)prop-2-enoate

HRID 1081628Notes

Reaction equation

HRID 1081628 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].[CH2:13](O)[CH3:14]>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]([O:9][CH2:13][CH3:14])=[O:8])[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 362513-(3-Bromophenyl)acrylic acid

Product 1

HCID 568440Ethyl 3-(3-bromophenyl)prop-2-enoate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

Under a nitrogen atmosphere, a stirred solution of 10.1 grams (0.045 mole) of 3-bromocinnamic acid and 40 drops of concentrated sulfuric acid in 75 mL of ethanol was heated at reflux for about 19 hours. After this time the reaction mixture was concentrated under reduced pressure to a residual oil. The oil was dissolved in methylene chloride, and the solution was washed with 50 mL of water and then with 50 mL of an aqueous solution saturated with sodium bicarbonate. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding about 11.4 grams of ethyl 3-(3-bromophenyl)-2-propenoate. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureat reflux for about 19 hours
  2. concentrationAfter this time the reaction mixture was concentrated under reduced pressure to a residual oil
  3. dissolutionThe oil was dissolved in methylene chloride
  4. washthe solution was washed with 50 mL of water
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5c4d59afb63c435fbd2af428257f391c
Source dataset
uspto-grants-1996_12
Patent number
US05587379

Reaction notes

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