Dimethylformamide → Acetyl chloride, (4-cyanophenoxy)-

HRID 520833Notes

Reaction equation

HRID 520833 reaction equation
[C:1]([C:3]1[CH:13]=[CH:12][C:6]([O:7][CH2:8][C:9](O)=[O:10])=[CH:5][CH:4]=1)#[N:2].C(Cl)(=O)C([Cl:17])=O.CN(C)C=O>ClCCl>[C:1]([C:3]1[CH:13]=[CH:12][C:6]([O:7][CH2:8][C:9]([Cl:17])=[O:10])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 7360972-(4-Cyanophenoxy)acetic acid

Product 1

HCID 12207748Acetyl chloride, (4-cyanophenoxy)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of commercially available 2-(4-cyanophenoxy)acetic acid (4.0 g, 22.6 mmol) in dichloromethane (80 mL) was added oxalyl chloride (2.17 mL, 24.8 mmol). To this mixture was added N,N-dimethylformamide (30 μL) dropwise and the mixture was stirred for 2 hours during which cessation of evolution of gas was observed. The resulting solution was diluted with dichloromethane (50 mL) and the solvent was removed under reduced pressure to provide the title compound as an oil which became a solid upon storing in the refrigerator.

Workup

  1. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-00020fe290904569b680f086c2c5b012
Source dataset
uspto-grants-2016_05
Patent number
US09328095B2

Reaction notes

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