Tetrahydro-4H-pyran-4-one → Tetrahydro-3,5-bis[(4-methoxy-2,3-dimethylphenyl)methylene]-4H-pyran-4-one

HRID 65674Notes

Reaction equation

HRID 65674 reaction equation
[O:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.[CH3:8][C:9]1[C:16]([CH3:17])=[C:15]([O:18][CH3:19])[CH:14]=[CH:13][C:10]=1[CH:11]=O>CCO.Cl>[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:10]([CH:11]=[C:3]2[C:4](=[O:7])[C:5](=[CH:11][C:10]3[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[C:16]([CH3:17])[C:9]=3[CH3:8])[CH2:6][O:1][CH2:2]2)=[C:9]([CH3:8])[C:16]=1[CH3:17]

Participants

5

Reactant 2

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 5960582,3-Dimethyl-p-anisaldehyde

Product 1

HCID 54006504Tetrahydro-3,5-bis[(4-methoxy-2,3-dimethylphenyl)methylene]-4H-pyran-4-oneYield 39%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A solution of 6.0 g (0.06 mole) of tetrahydro-4H-pyran-4-one, 21.6 g (0.13 mole) of 2,3-dimethyl-p-anisaldehyde in 75 ml of EtOH and 10 ml of concentrated HCl is stirred and heated at reflux for 3 hours. The product gradually precipitates during this period. After cooling, this material is filtered and treated with ether to give 9.1 g (39%) of yellow crystals, m.p. 225°-227°.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. customThe product gradually precipitates during this period
  4. temperatureAfter cooling
  5. filtrationthis material is filtered
  6. additiontreated with ether

Sources & evidence

ORD record
ord-7c34dea6c2764c90aec533e45a949a46
Source dataset
uspto-grants-1978_12
Patent number
US04128648

Reaction notes

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