2,2-Dimethylpentanoic acid → 2,2-Dimethylvaleroyl chloride

HRID 1109269Notes

Reaction equation

HRID 1109269 reaction equation
[CH3:1][C:2]([CH3:9])([CH2:6][CH2:7][CH3:8])[C:3](O)=[O:4].S(Cl)([Cl:12])=O>>[CH3:1][C:2]([CH3:9])([CH2:6][CH2:7][CH3:8])[C:3]([Cl:12])=[O:4]

Participants

3

Reactant 2

HCID 144552,2-Dimethylpentanoic acidHCID 24386Thionyl Chloride

Product 1

HCID 5191712,2-Dimethylvaleroyl chlorideYield 88.7%

Procedure

2,2-dimethyl valeric acid (49.0 g, 377 mmol) was added dropwise over 1 hour with stirring to freshly distilled thionyl chloride (102 g, 860 mmol) that was cooled in a water bath. After stirring for an additional 1/2 hour in a warm water bath, excess thionyl chloride was removed by distillation and the crude acid was then fractionally distilled to give 49.7 g of product that assayed >95% by gas chromatography, bp 45°/10.5 mm (lit. bp 45°/10 mm).

Workup

  1. temperaturewas cooled in a water bath
  2. customexcess thionyl chloride was removed by distillation
  3. distillationthe crude acid was then fractionally distilled

Sources & evidence

ORD record
ord-b5ee72f5d3f34620ab6e00580639cac8
Source dataset
uspto-grants-1994_06
Patent number
US05319133

Reaction notes

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