1,8-Cyclohexadecanedione → 8-Cyclohexadecen-1-one
Reaction equation
[C:1]1(=[O:17])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH:8]=[CH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(=O)CCCCCCCCC(=O)CCCCCC1>>[C:1]1(=[O:17])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH:9]=[CH:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1Participants
3
Procedure
7-Cyclohexadecen-1-one can be advantageously prepared from the known 1,8-cyclo-hexadecanedione by partial reduction and subsequent acid dehydration (a mixture of 7-cyclohexadecen-1-one and 8-cyclohexadecen-1-one is obtained). 8-Cyclohexadecen-1-one can be similarly obtained from the known 1,9-cyclohexadecanedione. A mixture of 1,8/1,9-cyclohexadecanediones can also be used and this is advantageous particularly for the preparation of the (E,Z)-7,8-cyclohexaden-1-one mixture. 1,8/1,9-cyclohexadecanediones are known for example from J. Org. Chem. 1968, 33, 4541 and U.S. Pat. No. 3,935,270.
Sources & evidence
- ORD record
- ord-12ce7157dc7843ea8d8f81395d7467d0
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07129380B2
Reaction notes
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