Malononitrile → Malononitrile, (p-(benzyloxy)benzylidene)-

HRID 362552Notes

Reaction equation

HRID 362552 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]([C:20]#[N:21])[C:18]#[N:19].N1CCCCC1>C(O)(C)C>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[C:17]([C:20]#[N:21])[C:18]#[N:19])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 8082PiperidineHCID 78109Benzaldehyde, 4-(phenylmethoxy)-

Product 1

HCID 33804Malononitrile, (p-(benzyloxy)benzylidene)-Yield 59.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

14.22 g (67 mmol) of 4-benzyloxybenzaldehyde and 5.31 g (80.4 mmol) of malonodinitrile were suspended in 80 ml of isopropanol in the presence of 0.2 ml of piperidine. In so doing the mixture increased in temperature from 19° to 31° C. A solution resulted, from which a solid was finally obtained. This was filtered off after stirring for 30 min. There were obtained 10.3 g (59%) of 2-(4-benzyloxy-benzylidene)-malononitrile with m.p. 146°-148° C.

Workup

  1. temperatureincreased in temperature from 19° to 31° C
  2. customA solution resulted, from which a solid
  3. customwas finally obtained
  4. filtrationThis was filtered off

Sources & evidence

ORD record
ord-c4dde75bb18e401392a0da866ad2d734
Source dataset
uspto-grants-1999_02
Patent number
US05869500

Reaction notes

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