Oxalyl chloride → 3-Cyclohexylprop-2-enoyl chloride

HRID 1512183Notes

Reaction equation

HRID 1512183 reaction equation
[CH:1]1([CH:7]=[CH:8][C:9]([OH:11])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C([Cl:15])=O>C(Cl)Cl.CN(C)C=O>[CH:1]1([CH:7]=[CH:8][C:9]([Cl:15])=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 2873483-Cyclohexylacrylic acid

Product 1

HCID 566232073-Cyclohexylprop-2-enoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-cyclohexyl-acrylic acid (5.0 g, 32.5 mmol) and oxalyl chloride (3.4 ml, 34.0 mmol) in anhydrous DCM (50 ml) was treated with one drop of dimethylformamide. The resulting solution was stirred at room temperature for 18 h, concentrated and used directly in the next step.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-809844e652754a09a33b33c3a53ace32
Source dataset
uspto-grants-2012_07
Patent number
US08217060B2

Reaction notes

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