Oxalyl chloride → HCID 19612333, compound

HRID 356700Notes

Reaction equation

[F:1][C:2]([F:12])([CH2:10][CH3:11])[C:3]([F:9])([F:8])[C:4]([OH:7])([F:6])[F:5].[C:13](Cl)(=[O:17])[C:14]([Cl:16])=[O:15]>>[C:14]([Cl:16])(=[O:15])[C:13]([O:7][C:4]([F:6])([F:5])[C:3]([F:8])([F:9])[C:2]([F:12])([F:1])[CH2:10][CH3:11])=[O:17]

Participants

Reactant 2

HCID 65578Oxalyl chloride2×

HCID 544183331,1,2,2,3,3-Hexafluoropentan-1-ol

Product 1

HCID 19612333HCID 19612333, compoundYield 52.8%

Procedure

In this example the product was prepared in two synthetic steps. In the first step hexafluoroamyl alcohol was reacted with 100% molar excess of oxalyl chloride. Upon completion of the reaction the excess oxalyl chloride was stripped from the product at reduced pressure to produce hexafluoroamyl chlorooxalate having an assay of 91.3% and in a corrected yield of 52.8%. In the second step hexafluoroamyl chlorooxalate was reacted with 2,5-dimethyl-2,5-dihydroperoxyhexane, in the presence of pyridine, to yield the product as described below:

Sources & evidence

ORD record: ord-a516f9b05d584aa59d7d1e6c8893db6c
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05837782

Reaction notes

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