p-Toluenesulfonic acid → HCID 13613731, compound

HRID 2387697Notes

Reaction equation

HRID 2387697 reaction equation
[CH2:1]([OH:9])[CH:2]([OH:8])[CH2:3][CH2:4][CH2:5][CH2:6]O.ClCCl.[C:13]1(C)[CH:18]=CC(S(O)(=O)=O)=C[CH:14]=1.S([O-])([O-])(=O)=[O:25].[Mg+2]>CC(C)=O>[CH3:14][C:13]1([CH3:18])[O:8][CH:2]([CH:3]([OH:25])[CH2:4][CH2:5][CH3:6])[CH2:1][O:9]1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 6344DichloromethaneHCID 78231,2,6-HexanetriolHCID 24083Sulfuric acid magnesium salt (1:1)

Product 1

HCID 13613731HCID 13613731, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 1,2,6-hexanetriol (10.0 g, 74.6 mmol) in acetone (50 ml) was added dichloromethane (50 ml), p-toluene sulphonic acid (1 mol %, catalyst) and anhydrous magnesium sulphate (50 g). The mixture was allowed to stir at ambient temperature for 24 hours. The MgSO4 was then removed via filtration and the acetone/dichloromethane solution washed with saturated sodium bicarbonate solution (1×30 ml) and water (2×30 ml). The organic solution was then dried over anhydrous MgSO4, filtered and solvent removed in vacuo, to yield the product as a colourless liquid. Yield=13.0 g (79%).

Workup

  1. customThe MgSO4 was then removed via filtration
  2. washthe acetone/dichloromethane solution washed with saturated sodium bicarbonate solution (1×30 ml) and water (2×30 ml)
  3. dry with materialThe organic solution was then dried over anhydrous MgSO4
  4. filtrationfiltered
  5. customsolvent removed in vacuo

Sources & evidence

ORD record
ord-39d00064ebe84f7daed606f0aa870e7b
Source dataset
uspto-grants-2012_09
Patent number
US08268959B2

Reaction notes

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