Diethyl Ether → HCID 136065541, compound

HRID 614108Notes

Reaction equation

HRID 614108 reaction equation
[Cl:1][CH:2]([Cl:6])[C:3](Cl)=[O:4].[OH:7][N:8]=[C:9]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=1)[C:10]([OH:12])=[O:11].CCOCC>C(Cl)Cl>[Cl:1][CH:2]([Cl:6])[C:3]([O:7][N:8]=[C:9]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=1)[C:10]([OH:12])=[O:11])=[O:4]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6593Dichloroacetyl chlorideHCID 136398790HCID 136398790, compound

Product 1

HCID 136065541HCID 136065541, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dichloroacetyl chloride (14.7 g.) was dissolved in methylene chloride (50 ml.). To the solution was added 2-hydroxyimino-2-(3-nitro-4-hydroxyphenyl)acetic acid (5.65 g.) (syn isomer) with stirring under ice-cooling. The solution was stirred for 30 minutes at room temperature after ether (10 ml.) was added. To the reaction mixture was added petroleum ether under ice-cooling. The precipitates were collected by filtration and thoroughly washed with petroleum ether to give 2-dichloroacetoxyimino-2-(3-nitro-4-hydroxyphenyl)acetic acid (syn isomer) (6.1 g.), which was used as a starting material for the following acylating reaction without further purification.

Workup

  1. temperaturecooling
  2. additionwas added
  3. temperaturecooling
  4. filtrationThe precipitates were collected by filtration
  5. washthoroughly washed with petroleum ether

Sources & evidence

ORD record
ord-3a62da11d7c4435c9575995644f2bc46
Source dataset
uspto-grants-1979_03
Patent number
US04143166

Reaction notes

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