4-Hydroxybenzaldehyde → Tyrphostin 8

HRID 2247789Notes

Reaction equation

HRID 2247789 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10](#[N:14])[CH2:11][C:12]#[N:13]>C(O)(C)C.N1CCCCC1>[C:12]([C:11]([C:10]#[N:14])=[CH:6][C:5]1[CH:8]=[CH:9][C:2]([OH:1])=[CH:3][CH:4]=1)#[N:13]

Participants

5

Reactant 2

HCID 1264-HydroxybenzaldehydeHCID 8010Malononitrile

Product 1

HCID 92970Tyrphostin 8Yield 69.8%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 3776IsopropanolSolvent

Procedure

3.7 g of p-hydroxybenzaldehyde and 2.3 g of malononitrile were dissolved in 10 ml of isopropanol followed by adding 1 drop of piperidine and reacted at 80° C. for 1 hour. Crystals were precipitated after cooling to the room temperature, collected by filtration and recrystallized from isopropanol to obtain 3.6 g of 4-(2,2'-dicyanovinyl)phenol as yellow crystals. Melting point=188-189.5° C.

Workup

  1. customreacted at 80° C. for 1 hour
  2. customCrystals were precipitated
  3. filtrationcollected by filtration
  4. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-7f47ca1df81c40f08e76d94ee57a9392
Source dataset
uspto-grants-1991_08
Patent number
US05037714

Reaction notes

Loading…