Acetic Acid → HCID 70619546, compound

HRID 1834669Notes

Reaction equation

HRID 1834669 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([C:13](=[O:17])[CH2:14][CH2:15][CH3:16])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7].C=O.Cl.[CH3:21][NH:22][CH3:23].[C:24](O)(=O)C>CCOCC.C(O)C>[ClH:1].[Cl:1][C:2]1[CH:12]=[C:11]([C:13](=[O:17])[CH:14]([CH2:21][N:22]([CH3:24])[CH3:23])[CH2:15][CH3:16])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 20373886HCID 20373886, compound

Product 1

HCID 70619546HCID 70619546, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

(2-Chloro-4-butyrylphenoxy)acetic acid (12.8 g., 0.05 mole), paraformaldehyde (1.65 g., 0.055 mole), dimethylamine hydrochloride (4.62 g., 0.056 mole) and acetic acid (1ml.) are combined and heated on a steam bath for three hours. The reaction mixture is treated with ethyl alcohol (75 ml.) and ether (125 ml.) which causes precipitation of 11.7 g. (69%) of [2-chloro-4-(2-dimethylaminomethylbutyryl)phenoxy]acetic acid hydrochloride which melts at 182° C. after recrystallization from 2-propanol (90 ml.).

Workup

  1. temperatureheated on a steam bath for three hours
  2. customprecipitation of 11.7 g
  3. custom(69%) of [2-chloro-4-(2-dimethylaminomethylbutyryl)phenoxy]acetic acid hydrochloride which melts at 182° C. after recrystallization from 2-propanol (90 ml.)

Sources & evidence

ORD record
ord-112a613bedaa42288de8daccbf7ece84
Source dataset
uspto-grants-1978_01
Patent number
US04070539

Reaction notes

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