p-Toluenesulfonic acid → 8-(3-Methylpentyloxy)octanol

HRID 36137

Reaction equation

HRID 36137 reaction equation
[CH3:1][CH:2]([CH2:6][CH3:7])[CH2:3][CH2:4][OH:5].[H-].[Na+].BrO.[C:12]1([CH3:22])[CH:17]=[CH:16][C:15](S(O)(=O)=O)=[CH:14][CH:13]=1.CN(C)[CH:25]=[O:26]>CO>[CH3:1][CH:2]([CH2:6][CH3:7])[CH2:3][CH2:4][O:5][CH2:22][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:25][OH:26]

Participants

7

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 6228DimethylformamideHCID 115083-Methyl-1-pentanolHCID 24758Sodium hydrideHCID 83547Hypobromous acid

Product 1

HCID 224079998-(3-Methylpentyloxy)octanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.67 gms of 3-methyl pentanol in 40 ml of dimethylformamide, 0.62 gms of sodium hydride are added; and the reaction mixture is stirred at room temperature for 1 hour. To this solution is added 4.0 gms of the protected bromo-alcohol and the reaction mixture is stirred at room temperature for 17 hours. The reaction mixture is then partitioned between ethyl acetate and water. The organic layer is washed with brine, dried over Na2SO4, filtered, and concentrated under vacuum to give a yellow liquid. To a solution of 4.0 gms of this liquid in 240 ml of methanol is added 0.40 gms of p-toluenesulfonic acid and the reaction is stirred at room temperature for 16 hours. The methanol is removed under reduced pressure, and the residue is partitioned between ethyl acetate and water. The organic layer is washed with aqueous NaHCO3 and brine, then dried over Na2SO4, filtered, and concentrated under vacuum to give 8-(3-methylpentyloxy)octanol.

Workup

  1. stirringthe reaction mixture is stirred at room temperature for 17 hours
  2. customThe reaction mixture is then partitioned between ethyl acetate and water
  3. washThe organic layer is washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customto give a yellow liquid
  8. stirringthe reaction is stirred at room temperature for 16 hours
  9. customThe methanol is removed under reduced pressure
  10. customthe residue is partitioned between ethyl acetate and water
  11. washThe organic layer is washed with aqueous NaHCO3 and brine
  12. dry with materialdried over Na2SO4
  13. filtrationfiltered
  14. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4365ea31456546e198c66696939c2a4c
Source dataset
uspto-grants-1995_05
Patent number
US05412137

Linked notes

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