Oxalyl chloride → 5-Cyclohexylpentanoyl chloride

HRID 1350268Notes

Reaction equation

HRID 1350268 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C([Cl:17])=O>CN(C)C=O.ClCCl>[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([Cl:17])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 94769Cyclohexanepentanoic acid

Product 1

HCID 152333055-Cyclohexylpentanoyl chlorideYield 100.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5-cyclohexylpentanoic acid (63.50 g, 345 mmol) in N,N-dimethylformamide (0.5 ml) and dichloromethane (350 ml) was cooled to 5° C. and treated dropwise with oxalyl chloride (31.6 ml, 362 mmol) over 30 minutes. The mixture was stirred at 0° C. for 3 hours then the solvent was removed under reduced pressure to afford 5-cyclohexylpentanoyl chloride as a pale yellow solid (70.0 g).

Workup

  1. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ba2ca54494384690bd3b62e089832082
Source dataset
uspto-grants-2007_05
Patent number
US07214694B2

Reaction notes

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