Acetone → HCID 136127060, compound

HRID 432057Notes

Reaction equation

HRID 432057 reaction equation
[C:1](Cl)(=[O:3])C.CO.CC(C)=[O:9].[CH3:11][O:12][N:13]=[C:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[O:16][C:15]1=NO>O>[OH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:14](=[N:13][O:12][CH3:11])[C:15]([O:3][CH3:1])=[O:9]

Participants

6

Reactant 4

HCID 180AcetoneHCID 887MethanolHCID 6367Acetyl chlorideHCID 178502623HCID 178502623, compound

Product 1

HCID 136127060HCID 136127060, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10.5 g of acetyl chloride (0.133 mol) are added dropwise to a mixture of 100 ml of methanol and 100 ml of acetone. 10 g (0.052 mol) of benzofuran-2,3-dione 3-(O-methyl-oxime) 2-oxime are dissolved in this mixture, and the reaction mixture is then stirred at room temperature for 12 hours. The mixture is poured into water and the product is extracted with ethyl acetate. The organic phase is washed with aqueous sodium bicarbonate solution and dried over sodium sulphate, and the solvent is distilled off under reduced pressure. This gives 9 g of crude product which, according to HPLC, contains 17.7% methyl E-2-(2-hydroxyphenyl)-2-methoxyimino-acetate of log p=1.48 and 61.8% methyl Z-2-(2-hydroxyphenyl)-2-methoxyimino-acetate of log p=2.38.

Workup

  1. extractionthe product is extracted with ethyl acetate
  2. washThe organic phase is washed with aqueous sodium bicarbonate solution
  3. dry with materialdried over sodium sulphate
  4. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-fbf6226af1a948dc9ead992ae083eff2
Source dataset
uspto-grants-2003_12
Patent number
US06660872B1

Reaction notes

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