Acetone → HCID 58550327, compound

HRID 2068874Notes

Reaction equation

HRID 2068874 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1([CH3:20])[CH2:19][CH2:18][CH2:17][C:12]2(OCC[O:13]2)[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=O.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>O.C(OCC)(=O)C>[CH2:1]([O:8][CH2:9][C:10]1([CH3:20])[CH2:19][CH2:18][CH2:17][C:12](=[O:13])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 58550271HCID 58550271, compound

Product 1

HCID 58550327HCID 58550327, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 7-benzyloxymethyl-7-methyl-1,4-dioxaspiro[4.5]decane (5.3 g, 19 mmol) in a mixed solvent of acetone (42 ml) and water (11 ml) was added pyridinium p-toluenesulfonate (4.8 g, 19 mmol), and the mixture was stirred with heating at 80° C. for 2 hr. After cooling, to the reaction mixture were added ethyl acetate and water, and the organic layer was separated. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were washed successively with water and saturated brine, and dried over sodium sulfate. Sodium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography to give the title compound (3.9 g, yield 88%).

Workup

  1. temperatureAfter cooling, to the reaction mixture
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe combined organic layers were washed successively with water and saturated brine
  5. dry with materialdried over sodium sulfate
  6. customSodium sulfate was removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-68e95e3544c843a091da6a6a4c78f276
Source dataset
uspto-grants-2012_10
Patent number
US08299070B2

Reaction notes

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