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Toluene → HCID 178444454, compound

HRID 2226073
Notes
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Reaction equation

HRID 2226073 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][CH2:14][CH2:15][C@H:16]2[CH2:21][CH2:20][C@H:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:18][CH2:17]2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].C1(C)C=CC=CC=1.[H][H]>[Pd].C(OCC)(=O)C>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]2[CH2:21][CH2:20][C@H:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:18][CH2:17]2)=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 1140TolueneHCID 178418361HCID 178418361, compoundHCID 178444453HCID 178444453, compound

Product 1

HCID 178444454HCID 178444454, compoundYield 83.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857
Ethyl Acetate
Solvent

Procedure

A mixture of 19 g of 1-butyloxy-4-[4-(trans-4-pentyl-cyclohexyl)-1-butenyl]benzene (cis/trans mixture), 200 ml of absolute toluene and 100 ml of absolute ethyl acetate: was treated with 2 g of palladium/carbon (10%) and hydrogenated at normal pressure and room temperature until the hydrogen uptake came to a standstill. The inorganic material was removed by filtration and the filtrate was concentrated. The residue was purified by chromatography on silica gel with toluene/ethyl acetate. Recrystallization from ethanol gave 16 g of pure 1-butyloxy-4-[4-(trans-4-pentylcyclohexyl)-l-butyl]benzene with m.p. (C-SB) 29° C. and cl.p. (SB --I) 43° C.

Workup

  1. customThe inorganic material was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by chromatography on silica gel with toluene/ethyl acetate
  4. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-affb223c7d2649b4b8df6fceb7dd6192
Source dataset
uspto-grants-1994_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05346647

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes