Acetic Acid → HCID 14098152, compound

HRID 569297Notes

Reaction equation

HRID 569297 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, compoundYield 48.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2,3-Dichloro-4-(4-chlorobutyryl)anisole (28.1 gm, 0.1 mole), dimethylamine hydrochloride (36.7 mg, 0.45 mole), paraformaldehyde (7.65 gm, 0.255 mole) and acetic acid (2.6 ml) were united, stirred and heated on a steam bath for 2 hours. N,N-dimethylformamide (100 ml) was added and the stirring and heating was continued for another two hours. The mixture was then poured into ice diluted to 800 ml with water and extracted with ether. The combined extracts were washed with water, dried over MgSO4 and evaporated in vacuo to give 14.2 gm of product, m.p. 58°-60° C.

Workup

  1. temperatureheated on a steam bath for 2 hours
  2. temperaturethe stirring and heating
  3. additionThe mixture was then poured into ice
  4. extractionextracted with ether
  5. washThe combined extracts were washed with water
  6. dry with materialdried over MgSO4
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-8026a72dbd014b068ae60c6d95ea9ab4
Source dataset
uspto-grants-1988_03
Patent number
US04731471

Reaction notes

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