Formaldehyde → 2,2-Dimethyl-3-methylene-6-cyano-4-chromanone

HRID 273749Notes

Reaction equation

HRID 273749 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:13]#[N:14])[CH:8]=2)[O:3]1.C=O.N1CCCC[CH2:19]1>C(O)C>[CH3:1][C:2]1([CH3:15])[C:11](=[CH2:19])[C:10](=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:13]#[N:14])[CH:8]=2)[O:3]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8082PiperidineHCID 109545982,2-Dimethyl-4-oxo-3,4-dihydro-2H-1-benzopyran-6-carbonitrile

Product 1

HCID 145179822,2-Dimethyl-3-methylene-6-cyano-4-chromanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 24 g of the chromanone, 12 g of paraformaldehyde and 24 ml of piperidine in 300 ml of ethanol is heated at 70° for 3 hours and evaporated. The residue is taken up in dichloromethane/petroleum ether 1:1, the mixture is filtered through silica gel and evaporated, and 2,2-dimethyl-3-methylene-6-cyano-4-chromanone is obtained as an unstable oil.

Workup

  1. customevaporated
  2. filtrationthe mixture is filtered through silica gel
  3. customevaporated

Sources & evidence

ORD record
ord-5fea985178994710ac11c8eecbb5ec1a
Source dataset
uspto-grants-1995_02
Patent number
US05387587

Reaction notes

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