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
3
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
- Patent number
- US05837782
Reaction notes
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