4-Propylcyclohexanone → HCID 178439285, compound

HRID 1731478Notes

Reaction equation

HRID 1731478 reaction equation
[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]2[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][CH3:18])[CH2:12][CH:11]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].C(C1CCC(=[O:28])CC1)CC.C(C1CCC([Mg]Br)CC1)CC>C1CCCCC1>[CH2:16]([C@H:13]1[CH2:14][CH2:15][C@H:10]([C:7]2([OH:28])[CH2:6][CH2:5][CH:4]([CH2:1][CH2:2][CH3:3])[CH2:9][CH2:8]2)[CH2:11][CH2:12]1)[CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 1424824-PropylcyclohexanoneHCID 178439119HCID 178439119, compoundHCID 178439192HCID 178439192, compound

Product 1

HCID 178439285HCID 178439285, compound

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

A solution in 300 ml of cyclohexane of 24.8 g of 1-(trans-4-propylcyclohexyl)-4-propylcyclohexene [obtainable by reacting 4-propylcyclohexanone with 4-propylcyclohexylmagnesium bromide to give 1-(trans-4-propylcyclohexyl)-4-propylcyclohexanol and dehydrating the latter] is hydrogenated over 4 g of 10% PdC at 20° and 1 bar until absorption of H2 ceases. The mixture is filtered and worked up analogously to Example 3 via the thiourea adduct to give trans,trans-4,4'-dipropylbicyclohexyl, c.p. 41°.

Sources & evidence

ORD record
ord-e53964b9d98f440196749dcdf887e99e
Source dataset
uspto-grants-1986_11
Patent number
US04622164

Reaction notes

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