Dimethylformamide → Nonanoyl chloride

HRID 1955423Notes

Reaction equation

HRID 1955423 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 17.67 g (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-664ade695f5f4a5187c745d5dadd8fb5
Source dataset
uspto-grants-2000_09
Patent number
US06124502

Reaction notes

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