Hydrogen Bromide → HCID 23041615, compound
Reaction equation
[CH2:1]([CH:6]1[CH2:11][CH2:10][CH:9]([C:12]23CCC(CCC)(CC2)C[CH2:13]3)[CH2:8][C:7]1=[O:23])[CH2:2]CCC.C(C1COC(=O)C1)(=O)C.[BrH:33]>>[C:7]([CH:6]([CH2:11][CH2:10][CH2:9][CH2:12][CH3:13])[CH2:1][CH2:2][Br:33])(=[O:23])[CH3:8]Participants
Procedure
A mixture of 33 g of 2-n-pentyl-5-(4-n-propylbicyclo[2.2.2]octyl)-cyclohexanone [obtainable by the method of P. Place et al., Tetrahedron 34, 1931 (1978) by reacting 3-acetylbutyrolactone with n-pentyl halide/NaH, subsequently reacting the product with hydrogen bromide to give 3-acetyl-1-bromo-n-octane, converting the latter into the corresponding ethylene ketal, reacting the corresponding Grignard compound with 4-cyano-1-n-propylbicyclo[2.2.2]octane and subsequently subjecting the product to an aldol condensation and catalytically hydrogenating the cyclohex-2-enone to give the target product], 20 ml of 80% hydrazine hydrate and 20 g of KOH in 240 ml of diethylene glycol is boiled under reflux for 2 hours. The reflux condenser is then replaced by a distillation column, the temperature is increased slowly to 200° C. and the mixture is kept at this temperature for 6 hours. After cooling, it is diluted with 300 ml of water, acidified and extracted with toluene. Customary working up of the organic phase gives 1-n-propyl-4-(trans-4-n-pentylcyclohexyl)-bicyclo[2.2.2]octane.
Sources & evidence
- ORD record
- ord-9179bf4814b84e2d8ffc477497b6f67a
- Source dataset
- uspto-grants-1987_11
- Patent number
- US04707295
Reaction notes
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