Dimethylformamide → 3-(2-Methylphenyl)propanoyl chloride

HRID 1359474

Reaction equation

HRID 1359474 reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH2:4][CH2:5][C:6](O)=[O:7].C(Cl)(=O)C([Cl:16])=O.CN(C)C=O>C(Cl)Cl>[CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH2:4][CH2:5][C:6]([Cl:16])=[O:7]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 309383-(2-Methylphenyl)propionic acidHCID 65578Oxalyl chloride

Product 1

HCID 130292013-(2-Methylphenyl)propanoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-methylhydrocinnamic acid (3.0 g, 18.3 mmole), oxalyl chloride (3.19 ml, 36.6 mmole) and methylene chloride (30 ml) was cooled in an ice bath and N,N-dimethylformamide (0.14 ml, 1.81 mmole) was added dropwise. The mixture was stirred at room temperature overnight. Concentration in vacuo gave 3-(2-methylphenyl)propanoyl chloride which was taken up in methylene chloride and used in the next step as a crude.

Workup

  1. temperaturewas cooled in an ice bath
  2. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-e73ff8e2d55a4b51a053c53a0659d534
Source dataset
uspto-grants-2003_07
Patent number
US06600015B2

Linked notes

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