Methanol → HCID 136127060, compound

HRID 432056Notes

Reaction equation

HRID 432056 reaction equation
[C:1](Cl)(=[O:3])C.C[OH:6].[CH3:7][O:8][N:9]=[C:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[O:12][C:11]1=NO>O>[OH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:10](=[N:9][O:8][CH3:7])[C:11]([O:3][CH3:1])=[O:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 6367Acetyl chlorideHCID 178502623HCID 178502623, compound

Product 1

HCID 136127060HCID 136127060, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5 g of acetyl chloride (0.064 mol) are added dropwise to 50 ml of methanol. 4.8 g (0.025 mol) of benzofuran-2,3-dione 3-(O-methyl-oxime) 2-oxime are dissolved in this mixture, and the reaction mixture is then heated under reflux for 12 hours. After cooling to room temperature, the mixture is poured into water and the product is extracted with diethyl ether. 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 4.33 g of crude product which, according to HPLC, contains 27.4% methyl E-2-(2-hydroxyphenyl)-2-methoxyimino-acetate of log p=1.48 and 56% methyl Z-2-(2-hydroxyphenyl)-2-methoxyimino-acetate of log p=2.37.

Workup

  1. temperaturethe reaction mixture is then heated
  2. temperatureunder reflux for 12 hours
  3. extractionthe product is extracted with diethyl ether
  4. washThe organic phase is washed with aqueous sodium bicarbonate solution
  5. dry with materialdried over sodium sulphate
  6. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-eede9af6374d4f108977cde411cff173
Source dataset
uspto-grants-2003_12
Patent number
US06660872B1

Reaction notes

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