2-Methylcyclohexanone → HCID 13549633, compound

HRID 384849Notes

Reaction equation

HRID 384849 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[O:8].[CH3:9][C@@H:10](O)[CH2:11][C@H:12]([OH:14])[CH3:13].C(=O)([O-])O.[Na+]>C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C1(C)C=CC=CC=1>[CH3:9][C@@H:10]1[CH2:11][C@@H:12]([CH3:13])[O:14][C:3]2([CH2:4][CH2:5][CH2:6][CH2:7][CH:2]2[CH3:1])[O:8]1

Participants

6

Reactant 3

HCID 114192-MethylcyclohexanoneHCID 516892Sodium BicarbonateHCID 27236832,4-Pentanediol, (-)-

Product 1

HCID 13549633HCID 13549633, compoundYield 77.7%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 1140TolueneSolvent

Procedure

A mixture of 2-methylcyclohexanone (13.1 g), (2R,4R)-2,4-pentanediol (12.2 g), pyridinium p-toluene sulfonate (119 mg) and toluene (120 ml) was refluxed with heating for 8 hours. The reaction mixture was added with a saturated aqueous solution of sodium hydrogen carbonate, extracted with diethyl ether, the organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: hexane/ethyl acetate=100/0 to 0/100 gradient) to obtain 18.0 g of (2R,4R)-2,4,7-trimethyl-1,5-dioxaspiro[5.5]undecane

Workup

  1. temperaturewas refluxed
  2. temperaturewith heating for 8 hours
  3. extractionextracted with diethyl ether
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (elution solvent: hexane/ethyl acetate=100/0 to 0/100 gradient)

Sources & evidence

ORD record
ord-203f9a7dea36498ea963dda58820237f
Source dataset
uspto-grants-2013_02
Patent number
US08367835B2

Reaction notes

Loading…