Hydrochloric Acid → 1,6-Diphenylhexane

HRID 1377221Notes

Reaction equation

HRID 1377221 reaction equation
O.[C:2]1([C:8](=O)[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=O)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[H][H]>[Pd].O1CCCC1.C(O)C>[C:2]1([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 769031,6-Diphenyl-1,6-hexanedioneHCID 178418361HCID 178418361, compound

Product 1

HCID 1368531,6-DiphenylhexaneYield 94.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a 2-liter three-necked flask equipped with a stirring device and a nitrogen substituting device, 5 g of a Pd-C catalyst (a 5% product, containing 55.9% of water) and a solution of 100.9 g of 1,6-diphenylhexane-1,6-dione in 400 milliliters of tetrahydrofuran and 400 milliliters of denatured ethanol as well as 5 milliliters of 6N-hydrochloric acid were introduced, stirred at a normal pressure and contacted with hydrogen gas. After absorption of hydrogen was stopped, the catalyst was filtered off and the solution was concentrated. The concentrate was dissolved in ethyl acetate, washed with a dilute aqueous solution of sodium hydrogencarbonate and water, and thereafter dried with anhydrous sodium sulfate. After removing off the solvent by a rotary evaporator, a distillation under a decreased pressure was carried out, to obtain 85.3 g of 1,6-diphenylhexane as colorless liquid.

Workup

  1. customIn a 2-liter three-necked flask equipped with a stirring device
  2. additionwere introduced
  3. customAfter absorption of hydrogen
  4. filtrationthe catalyst was filtered off
  5. concentrationthe solution was concentrated
  6. dissolutionThe concentrate was dissolved in ethyl acetate
  7. washwashed with a dilute aqueous solution of sodium hydrogencarbonate and water
  8. dry with materialdried with anhydrous sodium sulfate
  9. customAfter removing off the solvent
  10. customby a rotary evaporator
  11. distillationa distillation under a decreased pressure

Sources & evidence

ORD record
ord-ee53aaf8e1de4a32b2f39af9f74ccefb
Source dataset
uspto-grants-1997_09
Patent number
US05663440

Reaction notes

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