Acetic Acid → HCID 12395551, compound

HRID 1283249Notes

Reaction equation

HRID 1283249 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([O:9][CH3:10])[CH:5]=[CH:4][C:3]=1[C:11](=[O:16])[CH2:12][CH:13]([CH3:15])[CH3:14].C=O.Cl.[CH3:20]NC.C(O)(=O)C>C1C=CC=CC=1.CN(C=O)C>[CH2:20]=[C:12]([CH:13]([CH3:14])[CH3:15])[C:11]([C:3]1[CH:4]=[CH:5][C:6]([O:9][CH3:10])=[C:7]([Cl:8])[C:2]=1[Cl:1])=[O:16]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 12395546HCID 12395546, compound

Product 1

HCID 12395551HCID 12395551, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6228DimethylformamideSolvent

Procedure

A stirred mixture of 2',3'-dichloro-4'-methoxyisovalerophenone (261.6 g., 1.0 mole), paraformaldehyde (75.0 g., 2.5 mole), dimethylamine hydrochloride (327 g., 4.0 mole) and acetic acid (26 ml.) is heated on a steam bath for 18 hours, treated with DMF (500 ml.), heated an additional 3 hours, then poured into ice water (1.7 l.). The crude product which separates is dissolved in benzene (600 ml.) and dried over sodium sulfate. Evaporation of the benzene affords 237 g. of 2-methylene-2',3'-dichloro-4'-methoxyisovalerophenone which melts at 46°-51°C. and is used in Step C without further purification.

Workup

  1. temperatureis heated on a steam bath for 18 hours
  2. temperatureheated an additional 3 hours
  3. dry with materialdried over sodium sulfate
  4. customEvaporation of the benzene
  5. customaffords 237 g
  6. customof 2-methylene-2',3'-dichloro-4'-methoxyisovalerophenone which melts at 46°-51°C. and is used in Step C without further purification

Sources & evidence

ORD record
ord-0253032bf10a40a4bc23a47596215cf4
Source dataset
uspto-grants-1976_08
Patent number
US03974212

Reaction notes

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