Oxalyl chloride → 4-(Cyclohexylmethyloxy)-3-nitrobenzoyl chloride

HRID 363035Notes

Reaction equation

HRID 363035 reaction equation
[CH:1]1([CH2:7][O:8][C:9]2[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][C:10]=2[N+:18]([O-:20])=[O:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C([Cl:24])=O>CN(C=O)C.C(Cl)Cl>[CH:1]1([CH2:7][O:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([Cl:24])=[O:14])=[CH:11][C:10]=2[N+:18]([O-:20])=[O:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 432168004-(Cyclohexylmethyloxy)-3-nitrobenzoic acid

Product 1

HCID 539599654-(Cyclohexylmethyloxy)-3-nitrobenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 21-3 (0.307 g, 1.1 mmol) and DMF (1 drop) in methylene chloride (3 ml) under nitrogen cooled in an ice-bath was added dropwise a solution of oxalyl chloride (0.113 ml, 1.3 mmol) in methylene chloride (1 ml). The resulting solution was stirred 1 h with ice-bath cooling, 1 h at ambient temperature, then was evaporated at reduced pressure to give crude 4-(cyclohexylmethyloxy)-3-nitrobenzoyl chloride as an oil.

Workup

  1. temperaturecooled in an ice-bath
  2. customwas evaporated at reduced pressure

Sources & evidence

ORD record
ord-c1042cfccc604c378fd78d86f414f712
Source dataset
uspto-grants-1999_02
Patent number
US05872138

Reaction notes

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