Oxalyl chloride → HCID 19612334, compound

HRID 356701Notes

Reaction equation

[C:1]([O:5][O:6][C:7]([CH3:13])([CH3:12])[CH2:8][CH:9]([CH3:11])[OH:10])([CH3:4])([CH3:3])[CH3:2].[C:14](Cl)(=[O:18])[C:15]([Cl:17])=[O:16]>>[C:15]([Cl:17])(=[O:16])[C:14]([O:10][CH:9]([CH3:11])[CH2:8][C:7]([O:6][O:5][C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:12])[CH3:13])=[O:18]

Participants

Reactant 2

HCID 65578Oxalyl chloride2×

HCID 220654633-t-Butylperoxy-1,3-dimethylbutanol

Product 1

HCID 19612334HCID 19612334, compoundYield 98.5%

Procedure

In this example the product was prepared in two synthetic steps. In the first step 3-t-butylperoxy-1,3-dimethylbutanol 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 3-t-butylperoxy-1,3-dimethylbutyl chlorooxalate having an assay of 97.5% and in a corrected yield of 98.5%. In the second step 3-t-butylperoxy-1,3-dimethylbutyl 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-b2e0af4702314b298dcaeac2ef7eec95
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05837782

Reaction notes

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