Ethanol → HCID 53950759, compound

HRID 2398126Notes

Reaction equation

HRID 2398126 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]([Cl:19])=[CH:15][CH:14]=1)[C:10]([OH:12])=[O:11].CCO>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]([Cl:19])=[CH:15][CH:14]=1)[C:10]([OH:12])=[O:11])=[O:4]

Participants

5

Reactant 3

HCID 702EthanolHCID 6593Dichloroacetyl chlorideHCID 126963670HCID 126963670, compound

Product 1

HCID 53950759HCID 53950759, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of dichloroacetyl chloride (1.8 ml.) in methylene chloride (15 ml.) was added 2-hydroxyimino-(4-chlorophenyl)acetic acid (anti-isomer) (1.5 g.) and the suspension stirred for two hours at room temperature. During this time most of the material dissolved. The solid was removed, washed with petroleum (b.p. 40°-60°) and the washings and filtrate were combined, kept at 5° overnight and the resulting solid was collected and dried to give the title acid (2.0 g; 85%), m.p. 80°, λmax. (EtOH) 258 nm (ε 12,280), νmax. (Nujol) 1774 (ester), 1750 and 1722 cm.-1 (CO2H).

Workup

  1. dissolutionDuring this time most of the material dissolved
  2. customThe solid was removed
  3. washwashed with petroleum (b.p. 40°-60°)
  4. waitkept at 5° overnight
  5. customthe resulting solid was collected
  6. customdried
  7. customto give the title acid (2.0 g; 85%), m.p. 80°, λmax

Sources & evidence

ORD record
ord-b5a131988d6b47a1996c583a29409e2c
Source dataset
uspto-grants-1977_05
Patent number
US04024134

Reaction notes

Loading…