Formaldehyde → HCID 70419362, compound

HRID 2413839Notes

Reaction equation

HRID 2413839 reaction equation
[Cl:1][C:2]1[C:12]([Cl:13])=[C:11]([C:14](=[O:16])[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.[CH3:23]C(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O>C(O)C>[ClH:1].[Cl:1][C:2]1[C:12]([Cl:13])=[C:11]([C:14](=[O:16])[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 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 123281882-(4-Acetyl-2,3-dichlorophenoxy)acetic acid

Product 1

HCID 70419362HCID 70419362, 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 hydrochoride (2.34 g, 0.03 mole), paraformaldehyde (1.05 g, 0.033 mol. equiv.) and glacial acetic (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-dimethylaminopropionyl)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-f9e1dd39198e492fb3854a4e2c079966
Source dataset
uspto-grants-1988_01
Patent number
US04719310

Reaction notes

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