Formaldehyde → 2,2-Dimethyltetrahydropyran-4-one

HRID 1823071Notes

Reaction equation

HRID 1823071 reaction equation
[O:1]=[C:2]([CH:4]=[C:5]([CH3:7])[CH3:6])[CH3:3].[CH2:8]=[O:9]>C(Cl)(Cl)Cl>[CH3:6][C:5]1([CH3:7])[CH2:4][C:2](=[O:1])[CH2:3][CH2:8][O:9]1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 8858Mesityl oxide

Product 1

HCID 17381592,2-Dimethyltetrahydropyran-4-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
165 °C

Procedure

Mesityl oxide (11.6 mmol) and aqueous formaldehyde (11.6 mmol) were combined and heated at 165° C. for 2 hours. The reaction mixture was cooled, partitioned between ethyl acetate and brine, dried over sodium sulfate and evaporated to an oil. The crude reaction product was subjected to flash column chromatography (silica gel) eluting with ethyl acetate-hexane (1:9) to give an oil. The oil was dissolved in chloroform (250 ml), amberlyst 15 resin (11 g) was added and the mixture stirred for about 16 hours. Filtration and evaporation yielded the crude product which was subjected to flash column chromatography (silica gel) eluting with diethyl ether-hexane (1:9) to give the desired product.

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between ethyl acetate and brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated to an oil
  5. customThe crude reaction product
  6. washeluting with ethyl acetate-hexane (1:9)
  7. customto give an oil
  8. filtrationFiltration and evaporation
  9. customyielded the crude product which
  10. washeluting with diethyl ether-hexane (1:9)

Sources & evidence

ORD record
ord-106eebdd9e2d4767a51800075964468a
Source dataset
uspto-grants-2006_05
Patent number
US07037936B2

Reaction notes

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