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

HRID 2260252Notes

Reaction equation

HRID 2260252 reaction equation
[Cl:1][C:2]1[C:9]([OH:10])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:13](OC(=O)C)(=[O:15])[CH3:14]>N1C=CC=CC=1>[C:13]([O:10][C:9]1[C:8]([O:11][CH3:12])=[CH:7][CH:6]=[C:3]([CH:4]=[O:5])[C:2]=1[Cl:1])(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 603956Chloroisovaniline

Product 1

HCID 144509932-Chloro-3-formyl-6-methoxyphenyl acetate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

26.0 g of 2-chloro-3-hydroxy-p-anisaldehyde are dissolved in 400 ml of acetic anhydride and 5 ml of pyridine. The solution is stirred at 80° for 8 hours, subsequently evaporated, the residue is partitioned between ice-water and methylene chloride, the organic phase is dried over sodium sulfate, evaporated and the residue is recrystallized from methylene chloride/petroleum ether. There is obtained 2-chloro-3-formyl-6-methoxyphenyl acetate of m.p. 48°-50°.

Workup

  1. customsubsequently evaporated
  2. customthe residue is partitioned between ice-water and methylene chloride
  3. dry with materialthe organic phase is dried over sodium sulfate
  4. customevaporated
  5. customthe residue is recrystallized from methylene chloride/petroleum ether

Sources & evidence

ORD record
ord-087a7bf45e4d40f5858053d1ec9c7914
Source dataset
uspto-grants-1995_12
Patent number
US05476875

Reaction notes

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