Oxalyl chloride → Methyl 9-chloro-9-oxononanoate

HRID 463748

Reaction equation

HRID 463748 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[CH3:7][O:8][C:9](=[O:20])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]CC(O)=O>C(Cl)(Cl)Cl>[CH3:7][O:8][C:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:1][C:2]([Cl:4])=[O:3])=[O:20]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 75009Monomethyl azelate

Product 1

HCID 544297Methyl 9-chloro-9-oxononanoate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

In a separate process, 23.9 g of azelaic monomethylester was dissolved in 30 ml chloroform. Oxalylchloride (15 ml) was added, all at once, and the mixture refluxed 2 hours at 50° C. The mixture was cooled; excess solvent and oxalylchloride were evaporated. After distillation, 25.8 g of CH3OCO(CH2)7COCl was obtained.

Workup

  1. temperatureThe mixture was cooled
  2. customexcess solvent and oxalylchloride were evaporated
  3. distillationAfter distillation

Sources & evidence

ORD record
ord-e70b7d36c96148e3b9e913f07b19395b
Source dataset
uspto-grants-1985_10
Patent number
US04544668

Linked notes

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