p-Toluenesulfonic acid → HCID 59714866, compound

HRID 2223863Notes

Reaction equation

HRID 2223863 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1([CH:10]([CH2:13][OH:14])[CH2:11][OH:12])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.CO[C:17](OC)([CH3:19])[CH3:18].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>CC(C)=O>[CH3:18][C:17]1([CH3:19])[O:12][CH2:11][CH:10]([C:4]2([CH2:3][CH2:2][OH:1])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]2)[CH2:13][O:14]1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 516892Sodium BicarbonateHCID 59714891HCID 59714891, compound

Product 1

HCID 59714866HCID 59714866, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-[1-(2-hydroxyethyl)cyclohexyl]propane-1,3-diol (200 mg) in acetone (10 mL) were added 2,2,-dimethoxypropane (206 mg) and p-toluenesulfonic acid (17 mg) at room temperature. After stirring the solution at room temperature for 48 hours, a saturated aqueous sodium bicarbonate solution was added thereto, and it was concentrated under reduced pressure. To the resulting residue were added diethyl ether and water, and it was extracted with diethyl ether. The organic layer was washed in turn with 0.5N hydrochloric acid, water and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=1:1 to 1:2) to give the title compound (190 mg).

Workup

  1. concentrationit was concentrated under reduced pressure
  2. additionTo the resulting residue were added diethyl ether and water, and it
  3. extractionwas extracted with diethyl ether
  4. washThe organic layer was washed in turn with 0.5N hydrochloric acid, water and saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=1:1 to 1:2)

Sources & evidence

ORD record
ord-e63b07363b164642b34d4f0dc146ca69
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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