Sodium Bicarbonate → 3-(10-Hydroxydecyl)-4-methyl-2-cyclohexene-1-one

HRID 1375124Notes

Reaction equation

HRID 1375124 reaction equation
C1CO[C:3]2([CH2:8][CH2:7][CH:6]([CH3:9])[C:5]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][OH:29])(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:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][C:5]1[CH:6]([CH3:9])[CH2:7][CH2:8][C:3](=[O:2])[CH:4]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 219991391,1-(Ethylenedioxy)-3-(10-hydroxydecyl)-4-methyl-3-(phenylsulfonyl)-cyclohexane

Product 1

HCID 106354973-(10-Hydroxydecyl)-4-methyl-2-cyclohexene-1-oneYield 75%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6212ChloroformSolvent

Procedure

Paratoluenesulfonic acid (20 ml) was added to a solution of 235 mg of 1,1-(ethylenedioxy)-3-(10-hydroxydecyl)-4-methyl-3-(phenylsulfonyl)-cyclohexane in 20 ml of chloroform and 4 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 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 while using hexane-ethyl acetate, whereby 3-(10-hydroxydecyl)-4-methyl-2-cyclohexene-1-one was obtained in the form of a colorless oil. Yield: 75%, CCM: (hexane-AcOEt: 6-4) Rf=0.2

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 distilled off under reduced pressure
  6. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-53199389c18941439e07949facfb6c19
Source dataset
uspto-grants-2007_01
Patent number
US07166642B1

Reaction notes

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