Potassium Hydroxide → HCID 13071115, compound

HRID 1605394Notes

Reaction equation

HRID 1605394 reaction equation
CS(O[CH:6]1[CH2:13][CH:12]2[CH2:14][CH:8]([O:9][CH:10]([CH2:15][O:16][S:17]([CH3:20])(=[O:19])=[O:18])[O:11]2)[CH2:7]1)(=O)=O.[OH-].[K+].C(=O)(O)[O-].[Na+]>C(O)(C)C>[CH3:20][S:17]([O:16][CH2:15][CH:10]1[O:11][CH:12]2[CH2:14][CH:8]([CH2:7][CH:6]=[CH:13]2)[O:9]1)(=[O:18])=[O:19]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 516892Sodium BicarbonateHCID 13071123HCID 13071123, compound

Product 1

HCID 13071115HCID 13071115, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

To a hot suspension of 280 mg of 7-methylsulphonyloxy-3-methylsulphonyloxymethyl-2,4-dioxabicyclo[3,3,1]nonane in 2,5 ml of isopropanol is added 2,5 ml of a boiling 2n potassium hydroxide solution in isopropanol while stirring vigorously, and the resulting reaction mixture is boiled under reflux for 3 minutes. The reaction mixture is cooled and treated with 5 ml of an 8% sodium bicarbonate solution, then extracted 3 times with methylene chloride. The combined extracts are dried over sodium sulphate and the solvent is distilled off in vacuo uner reduced pressure to leave as residue the racemic 3-methylsulphonyloxymethyl-2,4-dioxabicyclo[3,3,1]non-6-ene in the form of a colourless oil, which soon congeals to a crystalline solid (m.p. 53°-56°C).

Workup

  1. customthe resulting reaction mixture
  2. temperatureunder reflux for 3 minutes
  3. temperatureThe reaction mixture is cooled
  4. extractionextracted 3 times with methylene chloride
  5. dry with materialThe combined extracts are dried over sodium sulphate
  6. distillationthe solvent is distilled off in vacuo uner reduced pressure

Sources & evidence

ORD record
ord-42bc5780f93b4647af5dc4f76e801e60
Source dataset
uspto-grants-1976_04
Patent number
US03950362

Reaction notes

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