Sodium Bicarbonate → HCID 10824726, compound

HRID 1976742Notes

Reaction equation

HRID 1976742 reaction equation
C1CO[C:3]2([CH2:8][CH2:7][CH2:6][C:5]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28])(S(C3C=CC=CC=3)(=O)=O)[CH2:4]2)[O:2]1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.CC(C)=O>[OH:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][C:5]1[CH2:6][CH2:7][CH2:8][C:3](=[O:2])[CH:4]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 15521318HCID 15521318, compound

Product 1

HCID 10824726HCID 10824726, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6212ChloroformSolvent

Procedure

Paratoluenesulfonic acid (20 mg) was added to a solution of 193 mg of 1,1-(ethylenedioxy)-3-(10-hydroxydecyl)-3-(phenylsulfonyl)-cyclohexane in 3 ml of chloroform and 0.6 ml of acetone. To the resulting mixture was added 10 ml of a saturated aqueous solution of sodium bicarbonate, followed by extraction with dichloromethane. The organic layer was washed with saturated saline and dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column using hexane-ethyl acetate, whereby 86 mg of 3-(10-hydroxydecyl)-2-cyclohexen-1-one were obtained in the form of a colorless oil. Yield: 77%

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. washThe organic layer was washed with saturated saline
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-1c6b3a2126434d75b38903d6be2c8fe6
Source dataset
uspto-grants-2001_05
Patent number
US06228893B1

Reaction notes

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