Water → 2,2-Dimethyloxane-4-carbaldehyde

HRID 709805Notes

Reaction equation

HRID 709805 reaction equation
C[O:2][CH:3]=[C:4]1[CH2:9][CH2:8][O:7][C:6]([CH3:11])([CH3:10])[CH2:5]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1COCC1>[CH3:10][C:6]1([CH3:11])[CH2:5][CH:4]([CH:3]=[O:2])[CH2:9][CH2:8][O:7]1

Participants

5

Reactant 3

HCID 962Water2×HCID 6101p-Toluenesulfonic acidHCID 1308515744-(methoxymethylene)-2,2-dimethyltetrahydro-2H-pyran

Product 1

HCID 122319282,2-Dimethyloxane-4-carbaldehydeYield 60.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(methoxymethylene)-2,2-dimethyltetrahydro-2H-pyran (4.00 g) in THF (20 mL) were added water (8.0 mL) and p-toluenesulfonic acid (4.90 g), and the mixture was stirred at room temperature for 20 hr. To the reaction mixture was added water, and the mixture was extracted with diethyl ether. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (2.20 g) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-c451d367b39b4de1913e04567d3d323c
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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