Oxalyl chloride → (3-Acetoxy-4-nitro-phenyl)acetyl chloride

HRID 49713Notes

Reaction equation

HRID 49713 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH2:14][C:15]([OH:17])=O)[CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])(=[O:3])[CH3:2].C(Cl)(=O)C([Cl:21])=O>ClCCl.CN(C)C=O>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH2:14][C:15]([Cl:21])=[O:17])[CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 17946639(3-Acetoxy-4-nitro-phenyl)acetic acid

Product 1

HCID 17946635(3-Acetoxy-4-nitro-phenyl)acetyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of (3-acetoxy-4-nitro-phenyl)acetic acid (2.0 g, Reference Example 18) in dichloromethane (20 mL) was treated with a solution of oxalyl chloride in dichloromethane (4.4 mL, 2M) and then with dry dimethylformamide (1 drop). After a vigorous effervescence the mixture was stirred at room temperature for 4 hours, then evaporated to give the title compound as a viscous oil which was used immediately without further purification.

Workup

  1. customevaporated

Sources & evidence

ORD record
ord-38a960a949404cc781f662a03e992d71
Source dataset
uspto-grants-2004_03
Patent number
US06706738B2

Reaction notes

Loading…