Toluene → (S)-1-(4'-octyloxy-4-biphenylyloxy)-propan-2-ol

HRID 1074104Notes

Reaction equation

HRID 1074104 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.[O:25]1[CH2:29][CH2:28]CC1.[C:30]1(C)C=CC=CC=1>CN(C)C=O.O>[CH2:17]([O:16][C:13]1[CH:14]=[CH:15][C:10]([C:7]2[CH:6]=[CH:5][C:4]([O:3][CH2:30][C@@H:29]([OH:25])[CH3:28])=[CH:9][CH:8]=2)=[CH:11][CH:12]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

7

Reactant 4

HCID 1140TolueneHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 104943294-Hydroxy-4'-octyloxybiphenyl

Product 1

HCID 15041725(S)-1-(4'-octyloxy-4-biphenylyloxy)-propan-2-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of (2S)-2-(2'-tetrahydropyranyloxy)-1-(p-toluenesulfonyloxy)-propane (20 g) in N,N-dimethylformamide (hereinafter abbreviated to DMF) (300 ml) was added to a mixture of sodium hydride (60%) (2 g), 4-hydroxy-4'-octyloxy-biphenyl(10 g) and tetrahydrofuran (hereinafter abbreviated to THF) (200 ml), followed by agitating the resulting mixture at 60° C. for 4 hours, allowing it to cool down to room temperature, adding toluene (300 ml) and water (300 ml), separating the resulting organic layer, washing it with an alkali solution and then with water, concentrating it, adding ethanol (300 ml) and pyridium p-toluenesulfonate (hereinafter abbreviated to PPTS) (2 g), agitating the mixture at 50° C. for 3 hours, distilling off ethanol, adding toluene (300 ml), washing the resulting organic layer with water, concentrating it and recrystallizing the concentrate, to obtain (S)-1-(4'-octyloxy-4-biphenylyloxy)-propan-2-ol (8 g).

Workup

  1. temperatureto cool down to room temperature
  2. customseparating the resulting organic layer
  3. washwashing it with an alkali solution
  4. concentrationwith water, concentrating it
  5. additionadding ethanol (300 ml) and pyridium p-toluenesulfonate (hereinafter abbreviated to PPTS) (2 g)
  6. stirringagitating the mixture at 50° C. for 3 hours
  7. distillationdistilling off ethanol
  8. additionadding toluene (300 ml)
  9. washwashing the resulting organic layer with water
  10. concentrationconcentrating it
  11. customrecrystallizing the concentrate

Sources & evidence

ORD record
ord-234402a025d241d5ade7f332faa3b8dc
Source dataset
uspto-grants-1990_11
Patent number
US04973426

Reaction notes

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