Dichloromethane → 3(2H)-Benzofuranone, O-methyloxime

HRID 716729Notes

Reaction equation

HRID 716729 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3](=O)[CH2:2]1.Cl.[CH3:12][O:13][NH2:14].CC([O-])=O.[Na+].ClCCl>CO.O>[CH3:12][O:13][N:14]=[C:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[O:1][CH2:2]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 23556CoumaranoneHCID 517045Sodium AcetateHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 542716163(2H)-Benzofuranone, O-methyloximeYield 75%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of benzofuran-3(2H)-one (9) (100 g, 0.745 mol) in methanol (700 mL) was added O-methyl hydroxylamine hydrochloride (68.5 g, 0.820 mol) and NaOAc (67.3 g, 0.820 mol) at ambient temperature followed by heating to reflux for 1-3 h. The progress of the reaction was monitored by the HPLC analysis. Upon completion of the reaction, the inorganics were filtered off, and methanol was recovered from the filtrate to provide residue. The residue was subjected to extractive work-up using dichloromethane (500 mL) and water (1 L) followed by recovery of the organic layer to obtain the product meeting the desired specifications. Yield—75-83%.

Workup

  1. temperatureby heating
  2. temperatureto reflux for 1-3 h
  3. customUpon completion of the reaction
  4. filtrationthe inorganics were filtered off
  5. custommethanol was recovered from the filtrate
  6. customto provide residue
  7. customto obtain the product

Sources & evidence

ORD record
ord-6679a9da90c44d86a208779bbf299322
Source dataset
uspto-grants-2015_11
Patent number
US09193698B2

Reaction notes

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