HCID 178439118, compound → 4,4'‐Dipropyl‐1,1'‐bi(cyclohexane)

HRID 1731477Notes

Reaction equation

HRID 1731477 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([C@H:10]2[CH2:15][CH2:14][C@H:13]([CH2:16][CH2:17][CH3:18])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)[CH2:2][CH3:3]>C(O)C.O=[Pt]=O>[CH2:16]([CH:13]1[CH2:14][CH2:15][CH:10]([CH:7]2[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

4

Reactant 1

HCID 178439118HCID 178439118, compound

Product 1

HCID 186350684,4'‐Dipropyl‐1,1'‐bi(cyclohexane)

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A solution of 24.4 g of trans-1-p-propylphenyl-4-propylcyclohexane in 500 ml of ethanol is hydrogenated over 1 g of PtO2 for 1 hour at 60° and 100 bar, and the mixture is cooled, filtered and evaporated to give 4,4'-dipropylbicyclohexyl in the form of an oily mixture of isomers, which is taken up in 200 ml of boiling methanol. The resulting hot solution is poured into a boiling solution of 70 g of thiourea in 300 ml of methanol. The mixture is cooled to 0°, and the adduct which has been precipitated is filtered off and extracted by boiling with 300 ml of petroleum ether (b.p. 40°-60°). The undissolved residue is heated with 350 ml of 2N aqueous potassium hydroxide solution for 30 minutes at 50°. The solution is acidified with H2SO4 to give, after customary working up, trans,trans-4,4'-dipropylbicyclohexyl, c.p. 41°.

Workup

  1. temperature100 bar, and the mixture is cooled
  2. filtrationfiltered
  3. customevaporated

Sources & evidence

ORD record
ord-fd9c82609cef419dac5f08db504ba8f4
Source dataset
uspto-grants-1986_11
Patent number
US04622164

Reaction notes

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