4-tert-Butylcyclohexanol → 4-t-Butylcyclohexyl chlorooxalate
Reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[C:12](Cl)(=[O:16])[C:13]([Cl:15])=[O:14]>>[C:13]([Cl:15])(=[O:14])[C:12]([O:11][CH:8]1[CH2:7][CH2:6][CH:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:10][CH2:9]1)=[O:16]Participants
3
Procedure
In this example the product was prepared in two synthetic steps. In the first step 4-t-butylcyclohexanol 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 4-t-butylcyclohexyl chlorooxalate having an assay of 96.9% and in a corrected yield of 95.3%. In the second step 4-t-butylcyclohexyl chlorooxalate was reacted with 2,5-dimethyl-2,5-dihydroperoxyhexane, in the presence of pyridine, to yield the product:
Sources & evidence
- ORD record
- ord-75e2af5e52be4f0e9df3825b3c5143e7
- Source dataset
- uspto-grants-1998_11
- Patent number
- US05837782
Reaction notes
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