Acetic Acid → HCID 12395551, compound

HRID 1287437Notes

Reaction equation

HRID 1287437 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 three 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'-methoxyiosovalerophenone 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 three 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'-methoxyiosovalerophenone which melts at 46°-51° C. and is used in Step C without further purification

Sources & evidence

ORD record
ord-6d8090a79afb4d7da410723161112619
Source dataset
uspto-grants-1976_10
Patent number
US03984465

Reaction notes

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