Oxalyl chloride → 2-Chloro-2-oxoethyl hexanoate

Reaction equation

[C:1]([CH2:8][C:9]([OH:11])=[O:10])(=O)[CH2:2][CH2:3][CH2:4]CC.[C:12](Cl)(=O)[C:13]([Cl:15])=[O:14]>>[C:9]([O:11][CH2:12][C:13]([Cl:15])=[O:14])(=[O:10])[CH2:8][CH2:1][CH2:2][CH2:3][CH3:4]

Participants

Reactant 2

HCID 65578Oxalyl chloride

HCID 1288593-Oxooctanoic acid

Product 1

HCID 147665592-Chloro-2-oxoethyl hexanoate

Conditions

Temperature: 55 °C

Procedure

8.7 gm (0.05 mole) of hexanoylacetic acid and 12.7 gm (0.10 mole) of oxalyl chloride were mixed together at room temperature. The reaction was heated gradually over one hour at 50-60° C. for about two hours. Excess oxalyl chloride was removed under reduced pressure to yield an oil that exhibits no --OH stretch by IR. Weight was 9.6 gm.

Workup

customExcess oxalyl chloride was removed under reduced pressure
customto yield an oil that

Sources & evidence

ORD record: ord-66c59644c1aa45b0a34ad3780e11adf1
Source dataset: uspto-grants-1992_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05091560

Reaction notes

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