Acetic Acid → HCID 12395551, compound

HRID 597005Notes

Reaction equation

HRID 597005 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'-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 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'-methoxyisovalerophenone which melts at 46°-51° C. and is used in Step C without further purification

Sources & evidence

ORD record
ord-d96c545abf584ea3ba9b1a14897120cb
Source dataset
uspto-grants-1977_03
Patent number
US04012524

Reaction notes

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