Sodium Bicarbonate → HCID 10684188, compound

HRID 1375127Notes

Reaction equation

HRID 1375127 reaction equation
[CH3:1][C:2]1([CH3:32])[CH2:7][CH2:6][C:5]2(OCC[O:8]2)[CH2:4][C:3]1([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][OH:31])S(C1C=CC=CC=1)(=O)=O.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.CC(C)=O>[CH3:1][C:2]1([CH3:32])[CH2:7][CH2:6][C:5](=[O:8])[CH:4]=[C:3]1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][OH:31]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 21999135HCID 21999135, compound

Product 1

HCID 10684188HCID 10684188, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6212ChloroformSolvent

Procedure

Paratoluenesulfonic acid (20 mg) was added to a solution of 400 mg of 4,4-dimethyl-1,1-(ethylenedioxy)-3-(10-hydroxydecyl)-3-(phenylsulfonyl)-cyclohexane in 30 ml of chloroform and 6 ml of acetone. The resulting mixture was reacted at 50° C. for 24 hours. To the reaction mixture, were added 10 ml of a saturated sodium bicarbonate solution, followed by extraction with dichloromethane. The organic layer was washed with saturated saline and dried over magnesium sulfate. The solvent was then distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column while using hexane-ethyl acetate, whereby 4,4-dimethyl-3-(10-hydroxydecyl)-2-cyclohexen-1-one was obtained in the form of a colorless oil. Yield: 78%, TLC: (hexane-AcOEt: 6-4) Rf=0.25

Workup

  1. customThe resulting mixture was reacted at 50° C. for 24 hours
  2. extractionfollowed by extraction with dichloromethane
  3. washThe organic layer was washed with saturated saline
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was then distilled off under reduced pressure
  6. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-289e6366ccfc4da7866ac73211b4512d
Source dataset
uspto-grants-2007_01
Patent number
US07166642B1

Reaction notes

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