Water → 2-(2-Bromo-3-methylphenyl)acetic acid

HRID 1369594Notes

Reaction equation

HRID 1369594 reaction equation
[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][C:5]#N.S(=O)(=O)(O)[OH:13].[OH2:17]>C(OCC)C>[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][C:5]([OH:13])=[O:17]

Participants

5

Reactant 3

HCID 962Water2×HCID 1118Sulfuric AcidHCID 226726132-(2-Bromo-3-methylphenyl)acetonitrile

Product 1

HCID 183574462-(2-Bromo-3-methylphenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-bromo-3-methylbenzylcyanid (8.8 g, 42 mmol) was added to a mixture of conc sulfuric acid (50 ml) and water (60 ml) and was refluxed overnight. Water (150 ml) and diethyl ether were added and the organic layer was separated. To the organic layer was added a saturated sodium bicarbonate solution and the aqueous layer was separated. The aqueous layer was made acidic by addition of conc sulfuric acid. The acidic water solution was extracted with diethyl ether and the organic layer was washed with water, dried (Na2SO4) and evaporated under reduced pressure to give 6.5 g of the title compound.

Workup

  1. temperaturewas refluxed overnight
  2. customthe organic layer was separated
  3. additionTo the organic layer was added a saturated sodium bicarbonate solution
  4. customthe aqueous layer was separated
  5. additionThe aqueous layer was made acidic by addition of conc sulfuric acid
  6. extractionThe acidic water solution was extracted with diethyl ether
  7. washthe organic layer was washed with water
  8. dry with materialdried (Na2SO4)
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-412d421ae5e04513b37b3166611d2af2
Source dataset
uspto-grants-2003_06
Patent number
US06579884B1

Reaction notes

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