HCID 178494948, compound → HCID 178494949, compound

HRID 1609165Notes

Reaction equation

HRID 1609165 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([CH2:14][CH:15]=[CH:16][CH2:17][CH2:18][O:19][CH3:20])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1>C(OCC)(=O)C.[Ni]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[CH2:9][CH2:10][C@H:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH3:20])[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 178494948HCID 178494948, compound

Product 1

HCID 178494949HCID 178494949, compoundYield 62.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5.4 g of 1-chloro-4-[trans-4-(5-methoxy-2-pentenyl)cyclohexyl]benzene are dissolved in 80 ml of ethyl acetate in an autoclave, treated with 1 g of Raney nickel and hydrogenated for 7 hours at 60° C. and 5 kg/cm2. The suspension is filtered and evaporated. The residue (5.2 g) is crystallized twice from 30 ml of ethanol each time and gives 3.4 g of 1-chloro-4-[trans-4-(5-methoxypentyl)cyclohexyl]benzene; m.p. (C--I) 52.8° C.

Workup

  1. filtrationThe suspension is filtered
  2. customevaporated
  3. customThe residue (5.2 g) is crystallized twice from 30 ml of ethanol each time

Sources & evidence

ORD record
ord-997e276fa7dd44fb8438c8051ab16e17
Source dataset
uspto-grants-1995_03
Patent number
US05399689

Reaction notes

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