Sodium Hydroxide → 2-Cyano-3,3-diphenyl-2-propenoic acid

HRID 1758357Notes

Reaction equation

HRID 1758357 reaction equation
[C:1]1([C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:8]([C:14]#[N:15])[C:9]([O:11]CC)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO.O>[C:1]1([C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:8]([C:14]#[N:15])[C:9]([OH:11])=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 243274Etocrylene

Product 1

HCID 98378162-Cyano-3,3-diphenyl-2-propenoic acid

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
20 °C

Procedure

To 200 ml. of methanol:water (1:4) solution containing 55 g. (0.2 mole) of ethyl β,β-diphenyl-α-cyanoacrylate (CYASORB N-35, American Cyanamid), 18 g. of 50% NaOH (0.22 mole) is added and the soluton is stirred at about 20° C. overnight. After it is washed with ether, the aqueous solution is neutralized with dilute HCl to precipitate the product. The yield is 48 g., 97%, m.p., 207°-209° C.

Workup

  1. washAfter it is washed with ether
  2. customto precipitate the product
  3. custom97%, m.p., 207°-209° C.

Sources & evidence

ORD record
ord-2554c545361e402f855e186f59d661a8
Source dataset
uspto-grants-1983_02
Patent number
US04373060

Reaction notes

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