Benzyl Alcohol → benzyl chlorooxalate

Reaction equation

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

Participants

Reactant 2

HCID 244Benzyl Alcohol

HCID 65578Oxalyl chloride2×

Product 1

HCID 11019858benzyl chlorooxalateYield 92.1%

Procedure

In this example the product was prepared in two synthetic steps. In the first step benzyl 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 benzyl chlorooxalate having an assay of 96.6% and in a corrected yield of 92.1%. In the second step benzyl 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-3b33bdba8e36490c84e99bd7a4585c12
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05837782

Reaction notes

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