Acetic Acid → HCID 14098152, compound

HRID 569273Notes

Reaction equation

HRID 569273 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9](=[O:14])[CH2:10][CH2:11][CH2:12][Cl:13])[CH:5]=[CH:4][C:3]=1[O:15][CH3:16].Cl.[CH3:18]NC.C=O.C(O)(=O)C>O.CN(C)C=O>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9](=[O:14])[C:10](=[CH2:18])[CH2:11][CH2:12][Cl:13])[CH:5]=[CH:4][C:3]=1[O:15][CH3:16]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 14098151HCID 14098151, compound

Product 1

HCID 14098152HCID 14098152, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2,3-Dichloro-4-(4-chlorobutyryl)anisole (28.1 g, 0.1 mole), dimethylamine hydrochloride (36.7 g, 0.45 mole) and paraformaldehyde (7.65 g, 0.255 mole) were united and glacial acetic acid (2.6 ml) added. The mixture was stirred and heated on a steam bath under anhydrous conditions for 2 hours. Then the mixture was treated with N,N-dimethylformamide and heating and stirring on a steam bath continued for another 2 hours. The mixture was poured into a mixture of crushed ice and water (800 ml) and extracted with ether.

Workup

  1. temperatureheated on a steam bath under anhydrous conditions for 2 hours
  2. temperatureheating
  3. stirringstirring on a steam bath
  4. extractionextracted with ether

Sources & evidence

ORD record
ord-b694a3429ec44d1abc6a47cdc2ede862
Source dataset
uspto-grants-1988_03
Patent number
US04731470

Reaction notes

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