Ethanol → HCID 59304073, compound

HRID 544810Notes

Reaction equation

HRID 544810 reaction equation
[CH2:1]([S:13][CH:14]([CH3:27])[CH2:15][C:16]([CH:18]1[C:23]([CH3:25])([CH3:24])[CH2:22][CH:21]=[CH:20][CH:19]1[CH3:26])=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].CC[OH:30]>CO.O>[CH2:1]([S:13]([CH:14]([CH3:27])[CH2:15][C:16]([CH:18]1[C:23]([CH3:24])([CH3:25])[CH2:22][CH:21]=[CH:20][CH:19]1[CH3:26])=[O:17])=[O:30])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 2

HCID 702EthanolHCID 593040721-Butanone, 3-(dodecylthio)-1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-

Product 1

HCID 59304073HCID 59304073, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 3-(dodecylthio)-1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-1-butanone (2.00 g; 5.10 mmol) in MeOH (20 ml) was added at 0° C. to a solution of NaIO4 (1.14 g, 5.30 mmol) in H2O (11 ml). The temperature was brought to room temperature and EtOH (30 ml) was added. The suspension was stirred for 15 h and title compound extracted (ether/brine). The organic phase was washed with aqueous NaHSO3, H2O, saturated aqueous NaHCO3, then brine, dried over Na2SO4, and concentrated. (16.2 g). Flash chromatography (cyclohexane/ethyl acetate=7:3, then 1:1) on SiO2 (40 g) afforded 803 mg of the title compound (38%).

Workup

  1. customwas brought to room temperature
  2. extractiontitle compound extracted (ether/brine)
  3. washThe organic phase was washed with aqueous NaHSO3, H2O, saturated aqueous NaHCO3
  4. dry with materialbrine, dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d71cbefdad454d5a89446f851b291fce
Source dataset
uspto-grants-2011_05
Patent number
US07935669B2

Reaction notes

Loading…