Thionyl Chloride → Methyl 10-chloro-10-oxodecanoate

HRID 1655504Notes

Reaction equation

HRID 1655504 reaction equation
S(Cl)([Cl:3])=O.[C:5]([O:18][CH3:19])(=[O:17])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14](O)=[O:15]>>[C:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([Cl:3])=[O:15])([O:18][CH3:19])=[O:17]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 69957Monomethyl sebacate

Product 1

HCID 544219Methyl 10-chloro-10-oxodecanoate

Procedure

Thionyl chloride (360 g) was added dropwise to methyl hydrogen sebacate (432.6 g, 2 moles) at 60° C. with vigorous stirring and stirring was continued for 2 h under reflux. The reaction mixture was evaporated and the residue was distilled under reduced pressure to give the title compound as a colorless oil; yield: 400 g; bp 145°-150° C./4 mmHg. (Lit. bp 166°-168° C./14 mmHg; T. D. Heyes, J. C. Roberts, J. Chem. Soc., 1952, 4935).

Workup

  1. stirringstirring
  2. temperatureunder reflux
  3. customThe reaction mixture was evaporated
  4. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-efd51d9cc9874bd49f3a45fdc1f9024a
Source dataset
uspto-grants-1993_10
Patent number
US05250669

Reaction notes

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