Thionyl Chloride → 2-Methyldecanoyl chloride

HRID 1109273

Reaction equation

HRID 1109273 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][CH:6]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:7](O)=[O:8]>>[CH3:5][CH:6]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:7]([Cl:3])=[O:8]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 91167Decanoic acid, 2-methyl-

Product 1

HCID 190222792-Methyldecanoyl chlorideYield 99%

Conditions

Temperature
50 °C

Procedure

To thionyl chloride (93 g, 782 mmol), cooled to 15° C. in a water bath was added during 1 hour 2-methyl decanoic acid (64 g, 344 mmol). The cold water bath was removed and the mixture was heated at 50° C. with stirring for 45 minutes. The excess thionyl chloride was removed by distillation and the crude acid chloride was then fractionally distilled (b.p. 143°-45° C./5.8 mm) to give 69 g of product (99% yield) that showed an assay of >98% by GC.

Workup

  1. customThe cold water bath was removed
  2. customThe excess thionyl chloride was removed by distillation
  3. distillationthe crude acid chloride was then fractionally distilled (b.p. 143°-45° C./5.8 mm)

Sources & evidence

ORD record
ord-82e420d140904fdd82e493decce56dad
Source dataset
uspto-grants-1994_06
Patent number
US05319133

Linked notes

Loading…