4-Acetylbutyric acid → HCID 13839457, compound

HRID 1704698Notes

Reaction equation

HRID 1704698 reaction equation
[O:1]=[C:2]([CH3:9])[CH2:3][CH2:4][CH2:5][C:6](O)=[O:7].S(Cl)([Cl:12])=O>>[O:1]=[C:2]([CH3:9])[CH2:3][CH2:4][CH2:5][C:6]([Cl:12])=[O:7]

Participants

3

Reactant 2

HCID 184074-Acetylbutyric acidHCID 24386Thionyl Chloride

Product 1

HCID 13839457HCID 13839457, compoundYield 41.7%

Procedure

A mixture of 5.50 g of 5-ketohexanoic acid commercially available from Aldrich Chemical Co., Milwaukee, Wisconsin, and 8.83 g of thionyl chloride was stirred for 16 hours at 25° C. under argon. The reaction mixture was distilled to produce 2.62 g of the hexanoylchloride as a light-yellow oil; bp 99°-104° C. (aspirator vacuum), which was contaminated with about 60% of 4-chloro-5-ketohexanoyl chloride. The material had the following spectral chracteristics: nmr δ 1.90 (s, 3, COCH3), 2.0 (s, 3, CHClCOCH3), 5.10 (broad t, 1, CHClCOCH3); no signal for CO2H observed; IR λ max 5.70, 7.50, 8.10, 8.70, 9.45μ.

Workup

  1. distillationThe reaction mixture was distilled

Sources & evidence

ORD record
ord-272852b56f544826a0ac93f671cf4590
Source dataset
uspto-grants-1978_11
Patent number
US04127612

Reaction notes

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