HCID 178418361, compound → HCID 178444397, compound

HRID 1380778Notes

Reaction equation

HRID 1380778 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH:24]=[CH:25][C@H:26]4[CH2:31][CH2:30][C@H:29]([CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:28][CH2:27]4)=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[H][H]>[Pd].C1(C)C=CC=CC=1.C(O)C>[CH2:1]([C@H:6]1[CH2:7][CH2:8][C@H:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C@H:26]4[CH2:31][CH2:30][C@H:29]([CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:28][CH2:27]4)=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)[CH2:10][CH2:11]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178444396HCID 178444396, compound

Product 1

HCID 178444397HCID 178444397, compoundYield 70.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21863594Toluene ethanolSolvent

Procedure

2.20 g of 4-(trans-4-pentylcyclohexyl)-4'-[2-(trans-4-pentylcyclohexyl)vinyl]biphenyl were suspended in a toluene/ethanol mixture (3:2) in a sulphonation flask, treated with 200 mg of palladium/carbon (10%) and hydrogenated at normal pressure and 50° C. until the hydrogen uptake came to a standstill. Filtration of the mixture and concentration of the filtrate gave a white, semi-crystalline residue which, after recrystallization from 100 ml of hexane, yielded 1.55 g of 4-(trans-4-pentylcyclohexyl)-4'-[2-(trans-4-pentylcyclohexyl)ethyl]biphenyl as colourless needles; transition (presumably S-S) 219.5° C., transition S-N 243.2° C., cl.p. (N-I) 256.1° C. This substance showed itself to be very considerably super-coolable; it did not crystallize upon cooling to room temperature. Rf value (hexane): 0.32.

Workup

  1. filtrationFiltration of the mixture and concentration of the filtrate
  2. customgave a white, semi-crystalline residue which
  3. customafter recrystallization from 100 ml of hexane

Sources & evidence

ORD record
ord-a1681f30cf124cc7b7465b18fbcc569f
Source dataset
uspto-grants-1986_04
Patent number
US04583826

Reaction notes

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