Oxalyl chloride → 1-Phenylcyclohexanecarbonyl chloride

HRID 2375212

Reaction equation

HRID 2375212 reaction equation
[C:1]1([C:7]2([C:13]([OH:15])=O)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C([Cl:19])=O>ClCCl.CN(C)C=O>[C:1]1([C:7]2([C:13]([Cl:19])=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 708171-Phenylcyclohexane-1-carboxylic acid

Product 1

HCID 103535371-Phenylcyclohexanecarbonyl chlorideYield 102.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 1-phenylcyclohexanecarboxylic acid (E7) (0.095 g, 0.46 mmol) in dry dichloromethane (3 ml) under argon atmosphere at ice bath temperature oxalyl chloride (0.468 g, 3.68 mmol) and one drop of dimethylformamide were added. The reaction mixture was stirred at room temperature for 15 minutes and at 40° C. for one hour, then concentrated under reduced pressure to give crude title compound (0.105 g, ca. 100%). The crude product was immediately utilized in the next step of the synthesis without further purification.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9d333f9e30da4621922410ab2cc86c84
Source dataset
uspto-grants-2008_12
Patent number
US07465719B2

Linked notes

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