Acetic Acid → (3-Acetyl-5-bromo-4-hydroxy-phenyl)-acetic acid

HRID 983801Notes

Reaction equation

HRID 983801 reaction equation
[C:1]([C:4]1[CH:5]=[C:6](CC#N)[CH:7]=[C:8]([Br:11])[C:9]=1[OH:10])(=[O:3])[CH3:2].OS(O)(=O)=O.O.[C:21]([OH:24])(=[O:23])[CH3:22]>>[C:1]([C:4]1[CH:5]=[C:6]([CH2:22][C:21]([OH:24])=[O:23])[CH:7]=[C:8]([Br:11])[C:9]=1[OH:10])(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 1118Sulfuric AcidHCID 22556946(3-Acetyl-5-bromo-4-hydroxy-phenyl)-acetonitrile

Product 1

HCID 22556967(3-Acetyl-5-bromo-4-hydroxy-phenyl)-acetic acidYield 47%

Procedure

(3-acetyl-5-bromo-4-hydroxy-phenyl)-acetonitrile 213 (6 g, 23.6, mmol) is refluxed in a mixture of 50 mL acetic acid, 5 mL conc. H2SO4 and 5 mL water for about 2-3 h. This refluxed mixture is cooled to ambient temperature and poured onto ice forming a solid. The solid is isolated and recrystallized from a ethanol-water mixture to yield (3-acetyl-5-bromo-4-hydroxy-phenyl)-acetic acid 214 in a 47% yield.

Workup

  1. additionpoured onto ice forming a solid
  2. customThe solid is isolated
  3. customrecrystallized from a ethanol-water mixture

Sources & evidence

ORD record
ord-67ec2c68a3054a77898e57dba29858ec
Source dataset
uspto-grants-2005_03
Patent number
US06867200B1

Reaction notes

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