Dichloroacetyl chloride → HCID 86733035, compound

HRID 1578363Notes

Reaction equation

HRID 1578363 reaction equation
[Cl:1][CH:2]([Cl:6])[C:3](Cl)=[O:4].[OH:7][N:8]=[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]1[CH2:15][C:16]([OH:18])=[O:17]>C(Cl)Cl>[Cl:1][CH:2]([Cl:6])[C:3]([O:7][N:8]=[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]1[CH2:15][C:16]([OH:18])=[O:17])=[O:4]

Participants

4

Reactant 2

HCID 6593Dichloroacetyl chlorideHCID 86733036HCID 86733036, compound

Product 1

HCID 86733035HCID 86733035, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of methylene chloride (45 ml) and dichloroacetyl chloride (10 ml) was added portionwise with stirring 2-hydroxyiminophenylacetic acid (synisomer) (5g) in portions over about 15 minutes. The reaction mixture became solid, and was stirred for 1 hour at room temperature after the addition was complete. The reaction was diluted with petroleum (b.p. 40°-60°), filtered, and the solid washed several times with petroleum spirit to remove residual acid chloride. The solid was dried under vacuum, giving 2-dichloroacetoxyiminophenylacetic acid (syn-isomer)(8.0g; 96%), m.p. 115°, νmax. (CHBr3) 3470 and 1750 (--CO2H), 1765 cm. -1 (ester), τ (CDCl3) values include 2.0 - 2.7 (multiplet; aromatic protons), 3.85 (singlet; CHCl2).

Workup

  1. additionafter the addition
  2. filtrationfiltered
  3. washthe solid washed several times with petroleum spirit
  4. customto remove residual acid chloride
  5. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-eb7288bc8eac41b7b740566a6c4e5fbc
Source dataset
uspto-grants-1976_02
Patent number
US03936443

Reaction notes

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