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Neopentyl alcohol → 2,2-Dimethylpropyl chloro(oxo)acetate

HRID 356697
Notes
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Reaction equation

HRID 356697 reaction equation
[CH2:1]([OH:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[C:7](Cl)(=[O:11])[C:8]([Cl:10])=[O:9]>>[C:8]([Cl:10])(=[O:9])[C:7]([O:6][CH2:1][C:2]([CH3:5])([CH3:4])[CH3:3])=[O:11]
ParticipantsProcedureSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 6404Neopentyl alcoholHCID 65578Oxalyl chloride2×

Product 1

HCID 196123272,2-Dimethylpropyl chloro(oxo)acetateYield 92.7%

Procedure

In this example the product was prepared in two synthetic steps. In the first step neopentyl 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 neopentyl chlorooxalate having an assay of 100% and in a corrected yield of 92.7%. In the second step neopentyl 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-a5664ebc0dbb44fc96eb46f12b32568e
Source dataset
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05837782

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes