Nitric Acid → 2-Chloro-3-formyl-6-methoxy-5-nitrophenyl acetate

HRID 2260253Notes

Reaction equation

HRID 2260253 reaction equation
[C:1]([O:4][C:5]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[C:7]([CH:13]=[O:14])[C:6]=1[Cl:15])(=[O:3])[CH3:2].[N+:16]([O-])([OH:18])=[O:17]>>[C:1]([O:4][C:5]1[C:10]([O:11][CH3:12])=[C:9]([N+:16]([O-:18])=[O:17])[CH:8]=[C:7]([CH:13]=[O:14])[C:6]=1[Cl:15])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 144509932-Chloro-3-formyl-6-methoxyphenyl acetate

Product 1

HCID 144509942-Chloro-3-formyl-6-methoxy-5-nitrophenyl acetate

Procedure

38 g of 2-chloro-3-formyl-6-methoxyphenyl acetate are introduced portionwise at -5° to -10° within 15 minutes into 150 ml of 98 percent nitric acid. After stirring at -5° for 30 minutes the reaction mixture is poured into 1.5 l of ice-water and extracted three times with 500 ml of methylene chloride. The combined organic phases are washed with ice-water, dried over sodium sulfate and evaporated. The residue is crystallized from ether. There is obtained 2-chloro-3-formyl-6-methoxy-5-nitrophenyl acetate of m.p. 84°-85°.

Workup

  1. extractionextracted three times with 500 ml of methylene chloride
  2. washThe combined organic phases are washed with ice-water
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue is crystallized from ether

Sources & evidence

ORD record
ord-63bfca411aa34cc08d7666149e8dc944
Source dataset
uspto-grants-1995_12
Patent number
US05476875

Reaction notes

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