1-(3,5-Dibromo-4-hydroxyphenyl)ethan-1-one → (E)-4-(3,5-dibromo-4-hydroxyphenyl)-4-oxobut-2-enoic acid

HRID 2061413Notes

Reaction equation

HRID 2061413 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([Br:9])[C:7]=1[OH:8].O.[C:14]([OH:18])(=[O:17])[CH:15]=O>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:10](=[O:12])/[CH:11]=[CH:15]/[C:14]([OH:18])=[O:17])[CH:5]=[C:6]([Br:9])[C:7]=1[OH:8]

Participants

4

Reactant 2

HCID 761581-(3,5-Dibromo-4-hydroxyphenyl)ethan-1-oneHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 59829196(E)-4-(3,5-dibromo-4-hydroxyphenyl)-4-oxobut-2-enoic acidYield 78.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1-(3,5-dibromo-4-hydroxyphenyl)ethanone (5.0 g, 17.01 mmol) and glyoxylic acid monohydrate (1.566 g, 17.01 mmol) in acetic acid (10 mL) was stirred and heated at reflux for 5 days. After this time, the precipitate formed was collected and recrystallised from toluene. This gave the title compound as a brown solid (4.674 g, 78%). 1H NMR δ (ppm) (DMSO-d6): 6.70 (1 H, d, J=15.45 Hz), 7.93 (1 H, d, J=15.46 Hz), 8.24 (2 H, s).

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 days
  3. customAfter this time, the precipitate formed
  4. customwas collected
  5. customrecrystallised from toluene

Sources & evidence

ORD record
ord-4372702b5f954647a3de7ee762843919
Source dataset
uspto-grants-2012_10
Patent number
US08283351B2

Reaction notes

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