Thionyl Chloride → 2-Methyl octanoic acid chloride

HRID 2372242Notes

Reaction equation

HRID 2372242 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][CH:6]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:7](O)=[O:8]>>[CH3:5][CH:6]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:7]([Cl:3])=[O:8]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 942512-Methyloctanoic acid

Product 1

HCID 128122322-Methyl octanoic acid chlorideYield 98.4%

Procedure

To 8.98 g (75.5 mmol) of thionyl chloride placed in a flask was added 8.93 g (56.4 mmol) of the above (+)-2-methyl octanoic acid with stirring at room temperature. Then, the mixture was stirred and reacted at room temperature for 10 minutes, at 30° C. for 20 minutes, at 40° C. for 30 minutes and at 70° C. for 2 hours. Thereafter, an excessive amount of thionyl chloride was distilled off to obtain 9.80 g (55.5 mmol, yield: 98%) of a light brown (+)-2-methyl octanoic acid chloride.

Workup

  1. stirringThen, the mixture was stirred
  2. customreacted at room temperature for 10 minutes, at 30° C. for 20 minutes, at 40° C. for 30 minutes and at 70° C. for 2 hours
  3. distillationThereafter, an excessive amount of thionyl chloride was distilled off

Sources & evidence

ORD record
ord-70a94b1912f2430d841171cb007af5aa
Source dataset
uspto-grants-1992_03
Patent number
US05098602

Reaction notes

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