Ammonia → 4,6-Dimethyl-3(2H)-benzofuranone

HRID 366989Notes

Reaction equation

HRID 366989 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([CH3:13])[CH:12]=1)[O:5][CH2:6][C:7](O)=[O:8].N>>[CH3:1][C:2]1[C:3]2[C:7](=[O:8])[CH2:6][O:5][C:4]=2[CH:10]=[C:11]([CH3:13])[CH:12]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 794053,5-Xylyloxyacetic acid

Product 1

HCID 5955994,6-Dimethyl-3(2H)-benzofuranoneYield 100%

Conditions

Temperature
50 °C

Procedure

A mix of polyphosphoric acid and 2-(3,5-dimethylphenoxy) acetic acid was heated at 50° C. for 8 hours. The mix was poured in ice, treated with ammonia until a pH 7 was obtained. The mix was extracted with methylenechloride and the organic phase was treated with a solution of bicarbonate, made anhydrous (Na2SO4) and freed from the solvent under reduced pressure, to produce 4,6-dimethyl-3-benzofuranone (40% conversion, 100% yield).

Workup

  1. additionThe mix was poured in ice
  2. customwas obtained
  3. extractionThe mix was extracted with methylenechloride
  4. additionthe organic phase was treated with a solution of bicarbonate

Sources & evidence

ORD record
ord-d71dace968f94e6cb5ed67b1e7c537b1
Source dataset
uspto-grants-2000_10
Patent number
US06133191

Reaction notes

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