Acetic Anhydride → 2-Chloro-3-cyano-6-methoxyphenyl acetate

HRID 2254759Notes

Reaction equation

HRID 2254759 reaction equation
[Cl:1][C:2]1[C:10]([OH:11])=[C:9]([O:12][CH3:13])[CH:8]=[CH:7][C:3]=1[CH:4]=[N:5]O.[C:14](OC(=O)C)(=[O:16])[CH3:15]>>[C:14]([O:11][C:10]1[C:9]([O:12][CH3:13])=[CH:8][CH:7]=[C:3]([C:4]#[N:5])[C:2]=1[Cl:1])(=[O:16])[CH3:15]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 737926492-Chloro-3-hydroxy-p-anisaldehyde oxime

Product 1

HCID 542254972-Chloro-3-cyano-6-methoxyphenyl acetate

Procedure

21 g of 2-chloro-3-hydroxy-p-anisaldehyde oxime are heated under reflux for 20 hours together with 400 ml of acetic anhydride. Thereupon, the reaction mixture is evaporated, the residue is treated with 300 ml of ice-water, stirred for 1 hour, decanted, the thus-cooled residue is partitioned between methylene chloride and water, the organic phase is dried over sodium sulfate, evaporated, the residue is dried in a high vacuum, chromatographed on 200 g of silica gel with methylene chloride and recrystallized from methylene chloride/petroleum ether. There is obtained 2-chloro-3-cyano-6-methoxyphenyl acetate of m.p. 97°-99°.

Workup

  1. customThereupon, the reaction mixture is evaporated
  2. additionthe residue is treated with 300 ml of ice-water
  3. customdecanted
  4. customthe thus-cooled residue is partitioned between methylene chloride and water
  5. dry with materialthe organic phase is dried over sodium sulfate
  6. customevaporated
  7. customthe residue is dried in a high vacuum
  8. customchromatographed on 200 g of silica gel with methylene chloride
  9. customrecrystallized from methylene chloride/petroleum ether

Sources & evidence

ORD record
ord-a4921161365f4d858d02db8407970511
Source dataset
uspto-grants-1993_08
Patent number
US05236952

Reaction notes

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