p-Toluenesulfonic acid → HCID 22723505, compound

HRID 1581834Notes

Reaction equation

HRID 1581834 reaction equation
[C:1]([C:3]([CH3:10])([CH3:9])[CH:4]([OH:8])[CH2:5][CH2:6][OH:7])#[N:2].[C:11]1(C)[CH:16]=CC(S(O)(=O)=O)=C[CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([C:3]([CH:4]1[CH2:5][CH2:6][O:7][C:11]([CH3:16])([CH3:12])[O:8]1)([CH3:10])[CH3:9])#[N:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 11430Potassium CarbonateHCID 22178188HCID 22178188, compound

Product 1

HCID 22723505HCID 22723505, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Optically active 4-cyano-4-methyl-3-hydroxy-1-pentanol (500 mg) was dissolved in acetone (5 mL) and p-toluenesulfonic acid (50 mg) and powder molecular sieve 4A (100 mg) were added. The mixture was stirred at room temperature for 1 hr. Thereto was added a powder of potassium carbonate to neutralize the reaction mixture, which was filtrated and concentrated under reduced pressure to give optically active 4-(1-cyano-1-methylethyl)-2,2-dimethyl-1,3-dioxane.

Workup

  1. filtrationwas filtrated
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-743f594fe36946818a945552995d36f1
Source dataset
uspto-grants-2004_05
Patent number
US06730803B2

Reaction notes

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