Acetic Acid → HCID 14099859, compound

HRID 569257Notes

Reaction equation

HRID 569257 reaction equation
[Cl:1][C:2]1[C:13]([Cl:14])=[C:12]([C:15](=[O:19])[CH2:16][CH2:17][CH3:18])[CH:11]=[CH:10][C:3]=1[O:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].Cl.[CH3:21]NC.C=O.C(O)(=O)C>CN(C)C=O>[Cl:1][C:2]1[C:13]([Cl:14])=[C:12]([C:15](=[O:19])[C:16](=[CH2:21])[CH2:17][CH3:18])[CH:11]=[CH:10][C:3]=1[O:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 13958732HCID 13958732, compound

Product 1

HCID 14099859HCID 14099859, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(2,3-Dichloro-4-butyrylphenoxy)propionic acid (6.65 g, 0.022 mole), dimethylamine hydrochloride (12 g, 0.15 mole), paraformaldehyde (2.3 g, 0.077 equiv.) and acetic acid (1 ml) were mixed and stirred while heating on a steam bath for 2.5 hours. N,N-dimethylformamide (25 ml) was added to the mixture and stirring and heating continued for another 1.5 hours. The mixture was poured into ice water (600 ml) and the precipitate that formed removed by filtration, washed with water and dried. After recrystallization from butyl chloride, 58 g 3-[2,3-dichloro-4-(2-methylenebutyryl)phenoxy]propionic acid remained.

Workup

  1. temperaturewhile heating on a steam bath for 2.5 hours
  2. stirringstirring
  3. temperatureheating
  4. customthe precipitate that formed
  5. customremoved by filtration
  6. washwashed with water
  7. customdried
  8. customAfter recrystallization from butyl chloride, 58 g 3-[2,3-dichloro-4-(2-methylenebutyryl)phenoxy]propionic acid

Sources & evidence

ORD record
ord-f5e344990dc541e99fc6221bb91443b6
Source dataset
uspto-grants-1988_03
Patent number
US04731473

Reaction notes

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