Hydrochloric Acid → 2-Cyano-3-(3,4-dihydroxyphenyl)-2-propenoic acid

HRID 439561Notes

Reaction equation

HRID 439561 reaction equation
[OH-].[Na+].[C:3]([CH2:5][C:6]([OH:8])=[O:7])#[N:4].[OH:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[OH:18])[CH:13]=O.Cl>>[C:3]([C:5](=[CH:13][C:12]1[CH:15]=[CH:16][C:17]([OH:18])=[C:10]([OH:9])[CH:11]=1)[C:6]([OH:8])=[O:7])#[N:4]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 87683,4-DihydroxybenzaldehydeHCID 9740Cyanoacetic acidHCID 14798Sodium Hydroxide

Product 1

HCID 20542-Cyano-3-(3,4-dihydroxyphenyl)-2-propenoic acid

Procedure

To 2N aqueous sodium hydroxide solution (175 ml, 350 mmol) heated at 60° C. were added cyanoacetic acid (7.2 g, 86.7 mmol) and 3, 4-dihydroxybenzaldehyde (12.0 g, 86.9 mmol), and the resulting mixture was stirred for 30 minutes. The reaction mixture was allowed to cool at room temperature and gradually mixed with dilute hydrochloric acid until the reaction mixture became acidic. The product was filtered and dried to give α-cyano-3, 4-dihydroxycinnamic acid (hereinafter referred to as "Compound A" (10.0 g, 56% in yield).

Workup

  1. filtrationThe product was filtered
  2. customdried

Sources & evidence

ORD record
ord-83702e63595e4e26b6951b6bf4ae4186
Source dataset
uspto-grants-1996_05
Patent number
US05514711

Reaction notes

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