Dimethylformamide → Nonanoyl chloride

HRID 1275401Notes

Reaction equation

HRID 1275401 reaction equation
[C:1]([OH:11])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].CN(C)C=O.C(Cl)(=O)C([Cl:20])=O>ClCCl>[C:1]([Cl:20])(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8158Nonanoic AcidHCID 65578Oxalyl chloride

Product 1

HCID 69819Nonanoyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 15.80 g (0.10 mol) of nonanoic acid in 150 mL of dichloromethane at 0° C. was added 0.1 mL of N,N-dimethylformamide and 9.59 mL (0.11 mol) of oxalyl chloride. The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was then concentrated in vacuo, diluted with hexanes and filtered. The filtrate was concentrated in vacuo to provide 17.67g (100%) of nonanoyl chloride which was used without further purification in the next step.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. additiondiluted with hexanes
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d3e371a70a2648e19943096a0188fff9
Source dataset
uspto-grants-2000_12
Patent number
US06160132

Reaction notes

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