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

HRID 1859034Notes

Reaction equation

HRID 1859034 reaction equation
C1C=[CH:3][C:4]2[O:11][CH2:10][CH2:9][C:7](=[O:8])[C:5]=2[CH:6]=1.[CH2:12]=O.[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>C(O)C>[CH3:12][C:4]1([CH3:3])[C:5](=[CH2:6])[C:7](=[O:8])[C:9]2[C:15](=[CH:16][CH:17]=[C:18]([C:19]#[N:14])[CH:10]=2)[O:11]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8082PiperidineHCID 68110Chromanone

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-4772a91b0cfe4253a1d101172ae04117
Source dataset
uspto-grants-2000_11
Patent number
US06153627

Reaction notes

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