Dimethylformamide → p-Chlorophenoxyacetyl chloride

HRID 537302Notes

Reaction equation

HRID 537302 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8](O)=[O:9])=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:16])=O.CN(C=O)C>C(Cl)Cl>[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8]([Cl:16])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 26229(4-Chlorophenoxy)acetic acidHCID 65578Oxalyl chloride

Product 1

HCID 77771p-Chlorophenoxyacetyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-chlorophenoxy acetic acid (9.32 g, 0.05 mol) in CH2Cl2 (150 mL) was added oxalyl chloride (32.5 mL, of 2M in CH2Cl2) and DMF (0.2 mL). The resulting mixture was stirred at rt overnight under Ar. The mixture was concentrated in vacuo to give 10.3 g (100%) of 56a as colorless oil. 1H NMR (60 MHz, CDCl3): δ 7.0-6.7 (m, 4H), 4.8 (s, 2H) ppm.

Workup

  1. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-5214bc46c72f4ae5ab15413da4ca3731
Source dataset
uspto-grants-2014_10
Patent number
US08859780B2

Reaction notes

Loading…