Benzene → HCID 178447868, compound

HRID 2081154Notes

Reaction equation

HRID 2081154 reaction equation
[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]=[C:17](F)[F:18])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].C1C=CC=CC=1.[H-].COCCO[Al+]OCCOC.[Na+].[H-]>C1(C)C=CC=CC=1>[F:18]/[CH:17]=[CH:16]/[C:13]1[CH:14]=[CH:15][C:10]([C@H:7]2[CH2:8][CH2:9][C@H:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6]2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 178447869HCID 178447869, compound

Product 1

HCID 178447868HCID 178447868, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To trans-4-propyl-[4-(2,2-difluoro-1-ethenyl)phenyl]cyclohexane (23.4 g, 0.089 mol) were gradually added benzene (50 ml) and a 70 wt. % toluene solution of sodium bis(2-methoxyethoxy)aluminum hydride (50 ml) at a reaction temperature of -5° C. or lower with stirring, followed by gradually raising the reaction temperature up to 0° C. over 20 minutes, pouring the reaction solution in ice water (500 ml), extracting the resulting product with toluene (300 ml), twice washing with 6N-HCl (300 ml), further washing with water till the aqueous layer became neutral, drying the toluene solution over anhydrous magnesium sulfate, filtering off the drying agent, distilling off toluene, dissolving the residue in heptane, purifying according to silica gel chromatography, vacuum-distilling (130° C., 1.2 mmHg), five times recrystallizing from a mixed solvent of heptane and ethanol (1:1) and drying to obtain the objective substance (2.66 g, 0.011 mol). This compound exhibited a CN point of 24° C. and an NI point of 70° C.

Workup

  1. extractionextracting the resulting product with toluene (300 ml)
  2. washtwice washing with 6N-HCl (300 ml)
  3. washfurther washing with water till the aqueous layer
  4. dry with materialdrying the toluene solution over anhydrous magnesium sulfate
  5. filtrationfiltering off the drying agent
  6. distillationdistilling off toluene
  7. dissolutiondissolving the residue in heptane
  8. custompurifying
  9. distillationvacuum-distilling (130° C., 1.2 mmHg), five times
  10. customrecrystallizing from a mixed solvent of heptane and ethanol (1:1)
  11. customdrying
  12. customto obtain the objective substance (2.66 g, 0.011 mol)
  13. customa CN point of 24° C.
  14. customan NI point of 70° C.

Sources & evidence

ORD record
ord-92b343fd8d644a08a123818ef55c098f
Source dataset
uspto-grants-1993_02
Patent number
US05183587

Reaction notes

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