tert-Butanol → tert-Butyl 2-chloro-2-oxoacetate

HRID 356699Notes

Reaction equation

[C:1](Cl)(=[O:5])[C:2]([Cl:4])=[O:3].[C:7]([OH:11])([CH3:10])([CH3:9])[CH3:8]>>[C:2]([Cl:4])(=[O:3])[C:1]([O:11][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5]

Participants

Reactant 2

HCID 6386tert-Butanol

HCID 65578Oxalyl chloride2×

Product 1

HCID 11126621tert-Butyl 2-chloro-2-oxoacetateYield 90.8%

Procedure

In this example the product was prepared in two synthetic steps. In the first step t-butyl alcohol was reacted with 50% molar excess of oxalyl chloride. Upon completion of the reaction the excess oxalyl chloride was stripped from the product at reduced pressure to produce t-butyl chlorooxalate having an assay of 100% and in a corrected yield of 90.8%. In the second step t-butyl 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-4769b234a16641108fe5fd9c16168dca
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05837782

Reaction notes

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