Acetic Acid → HCID 70453705, compound

HRID 1732170Notes

Reaction equation

HRID 1732170 reaction equation
[Cl:1][C:2]1[C:12]([Cl:13])=[C:11]([C:14](=O)[CH3:15])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7].Cl.[CH3:18][NH:19][CH3:20].C=O.[C:23](O)(=O)C>C(O)C>[ClH:1].[Cl:1][C:2]1[C:12]([Cl:13])=[C:11]([CH2:14][CH2:15][CH2:18][N:19]([CH3:23])[CH3:20])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 123281882-(4-Acetyl-2,3-dichlorophenoxy)acetic acid

Product 1

HCID 70453705HCID 70453705, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(2,3-Dichloro-4-acetylphenoxy)acetic acid (U.S. Pat. No. 3,453,312) (7.89 g, 0.03 mole), dimethylamine hydrochloride (2.34 g, 0.03 mole), paraformaldehyde (1.05 g, 0.033 mol. equiv.) and glacial acetic acid (1 ml) were combined and heated on a steam bath for two hours. The reaction mixture was treated with hot ethanol (50 ml) and then cooled. The white solid was separated by filtration, washed with ethanol, dried and recrystallized from a mixture of ethanol and ether to give [2,3-dichloro-4-(3-dimethylaminopropyl)phenoxy]acetic acid hydrochloride, m.p. 194°-196° C.

Workup

  1. temperatureheated on a steam bath for two hours
  2. temperaturecooled
  3. customThe white solid was separated by filtration
  4. washwashed with ethanol
  5. customdried
  6. customrecrystallized from a mixture of ethanol and ether

Sources & evidence

ORD record
ord-51d99c9f3e3c4ef78a63668818f114a4
Source dataset
uspto-grants-1986_11
Patent number
US04625047

Reaction notes

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