Toluene → (S)-1-butyloxy-2-(p-toluenesulfonyloxy)propane

HRID 1090031Notes

Reaction equation

HRID 1090031 reaction equation
[CH2:1]([O:5][CH2:6][C@@H:7]([OH:9])[CH3:8])[CH2:2][CH2:3][CH3:4].[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1.C1(C)C=CC=CC=1>N1C=CC=CC=1>[CH2:1]([O:5][CH2:6][C@@H:7]([O:9][S:16]([C:13]1[CH:14]=[CH:15][C:10]([CH3:20])=[CH:11][CH:12]=1)(=[O:18])=[O:17])[CH3:8])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 1140TolueneHCID 73974-Toluenesulfonyl chlorideHCID 54289557(S)-1-butyloxy-2-hydroxypropane

Product 1

HCID 54488326(S)-1-butyloxy-2-(p-toluenesulfonyloxy)propaneYield 162.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A mixture of this (S)-1-butyloxy-2-hydroxypropane (47.6 g, 0.36 mol) with anhydrous pyridine (300 g) was cooled with ice, followed by dropwise adding thereto a solution of p-toluenesulfonyl chloride (75.8 g, 0.20 mol) in pyridine (70 ml) at 0° C., agitating the mixture at room temperature for 3 hours, adding toluene (800 ml), agitating the mixture, several times washing the resulting organic layer with water, drying it over anhydrous magnesium sulfate and distilling off toluene to obtain (S)-1-butyloxy-2-(p-toluenesulfonyloxy)propane (93.1 g). A solution of 4-hydroxy-4'-octyloxybiphenyl (10 g, 0.017 mol) in THF (20 ml) was dropwise added to a mixture of sodium hydride (0.85 g, 0.035 mol) with THF (10 ml), followed by further dropwise adding a solution of the above (S)-1-butyloxy-2-(p-toluenesulfonyloxy)-propane (5.7 g, 0.02 mol) in DMF (10 ml), agitating the mixture at 60° C. for 4 hours, allowing it to cool down, adding toluene, agitating the mixture, washing with 6N-HCl, then with 2N-NaOH aqueous solution and further with water, drying over anhydrous magnesium sulfate, distilling off toluene and recrystallizing the residue from ethanol (100 ml) to obtain (R)-4-(2'-butyloxy-1'-methyl)ethyloxy-4'-octyloxybiphenyl (8.2 g) (m.p. 39.6° C.).

Workup

  1. temperaturewas cooled with ice
  2. additionby dropwise adding
  3. washwashing the resulting organic layer with water
  4. dry with materialdrying it over anhydrous magnesium sulfate
  5. distillationdistilling off toluene

Sources & evidence

ORD record
ord-efc71a77f78347e990b54b7c6d02ad6b
Source dataset
uspto-grants-1992_01
Patent number
US05080827

Reaction notes

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