Water → 3-Oxaspiro[5.5]undec-7-en-9-one

HRID 1615742Notes

Reaction equation

HRID 1615742 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH:7]=O)[CH2:3][CH2:2]1.[CH3:9][C:10]([CH:12]=[CH2:13])=[O:11].S(=O)(=O)(O)O.O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:5]1[C:4]2([CH2:7][CH2:9][C:10](=[O:11])[CH:12]=[CH:13]2)[CH2:3][CH2:2][O:1][CH2:6]1

Participants

7

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 6570Methyl vinyl ketone2×HCID 9964078Tetrahydro-2H-pyran-4-carboxaldehyde

Product 1

HCID 687636893-Oxaspiro[5.5]undec-7-en-9-one

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

5.00 g (43.8 mmol) tetrahydropyran-4-carboxaldehyde and 3.56 ml (43.9 mmol) methylvinylketone were boiled in 70 ml of toluene with 0.07 ml conc. sulphuric acid using a water separator. After 3 h another 3.56 ml methylvinylketone were added and the mixture was boiled for a further 3 h. After cooling the reaction mixture was taken up in ethyl acetate, washed with water, dried and concentrated by rotary evaporation.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-0d300904884a445fb9a2345f074cbfb4
Source dataset
uspto-grants-2014_07
Patent number
US08765763B2

Reaction notes

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