p-Toluenesulfonic acid → 2-Propanone, 1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]-

HRID 1029978

Reaction equation

HRID 1029978 reaction equation
C1O[C:5]([OH:9])([CH2:7][OH:8])[CH2:4][O:3][C:2]1([OH:12])[CH2:10]O.[O:13]1[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14]1.[C:19]1(C)[CH:24]=CC(S(O)(=O)=O)=C[CH:20]=1.ClCCl>CCCCCC.C(OCC)(=O)C.C(OCC)C>[O:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH:18]1[O:8][CH2:7][C:5](=[O:9])[CH2:4][O:3][CH:2]1[CH2:10][CH2:24][CH2:19][CH2:20][O:12]1

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 6344DichloromethaneHCID 80803,4-dihydro-2H-pyranHCID 4180364Dihydroxyacetone dimer

Product 1

HCID 110106602-Propanone, 1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]-

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

9.0 g of dihydroxyacetone dimer, 21.0 g of 3,4-dihydro-2H-pyran and a catalytic amount of p-toluenesulfonic acid were added to 70 ml of dichloromethane and stirred under ice-cooling for 3 hours. After the completion of the reaction, 150 ml of diethyl ether was added thereto. The mixture was then washed with a saturated aqueous solution of sodium hydrogencarbonate and dried over anhydrous magnesium sulfate. After distilling off the solvent, the oily residue thus obtained was subjected to chromatography wherein silica gel was employed as a carrier while hexane/ethyl acetate was employed as a mobile phase. Thus 16.5 g of 1,3-bis(2-tetrahydro-pyranyloxy)propan-2-one was obtained as a colorless viscous liquid.

Workup

  1. temperaturecooling for 3 hours
  2. additionwas added
  3. washThe mixture was then washed with a saturated aqueous solution of sodium hydrogencarbonate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter distilling off the solvent
  6. customthe oily residue thus obtained

Sources & evidence

ORD record
ord-b2dbd7a34dee46b58b73467fbbc6c501
Source dataset
uspto-grants-1992_04
Patent number
US05102895

Linked notes

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