Oxalyl chloride → 1-(4-Methoxyphenyl)cyclohexanecarbonyl chloride

HRID 2375211Notes

Reaction equation

HRID 2375211 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:15]([OH:17])=O)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C(Cl)(=O)C([Cl:21])=O>ClCCl.CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:15]([Cl:21])=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 819791-(4-Methoxyphenyl)cyclohexanecarboxylic acid

Product 1

HCID 27596461-(4-Methoxyphenyl)cyclohexanecarbonyl chlorideYield 101.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 1-(4-methoxyphenyl)-cyclohexanecarboxylic acid (E3) (0.075 g, 0.32 mmol) in dry dichloromethane (2 ml) under argon atmosphere at ice bath temperature oxalyl chloride (0.327 g, 2.57 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 product (0.082 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-66b309671c7549f5af54fa082938deee
Source dataset
uspto-grants-2008_12
Patent number
US07465719B2

Reaction notes

Loading…