Dichloroacetyl chloride → HCID 86733035, compound

HRID 1729970Notes

Reaction equation

HRID 1729970 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 fifteen minutes. The reaction mixture became solid, and was stirred for one 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-933d0dc56f114daca4b53751b4754c70
Source dataset
uspto-grants-1976_11
Patent number
US03991046

Reaction notes

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