HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Acetic Acid → 2-Cyano-3-(4-methylphenyl)prop-2-enoic acid

HRID 236540
Notes
Print preview

Reaction equation

HRID 236540 reaction equation
[C:1]1([CH3:9])[C:2](C=O)=[CH:3][CH:4]=[CH:5][CH:6]=1.[C:10]([CH2:12][C:13]([OH:15])=[O:14])#[N:11].[C:16](O)(=O)C.C([O-])(=O)C.[NH4+]>C(O)C>[C:10]([C:12](=[CH:9][C:1]1[CH:6]=[CH:5][C:4]([CH3:16])=[CH:3][CH:2]=1)[C:13]([OH:15])=[O:14])#[N:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 9740Cyanoacetic acidHCID 107222-MethylbenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 3140122-Cyano-3-(4-methylphenyl)prop-2-enoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Tolualdehyde (400 g), cyanoacetic acid (311 g), acetic acid (60 ml) and ammonium acetate (25.6 g) were refluxed for 4 hours by heating in ethyl alcohol (1.6 l). After the reaction, ethyl alcohol was concentrated to 600 ml under a reduced pressure, and it was poured in 1 liter of iced water to separate crystals. The separated crystals were filtered out by suction to obtain 2-cyano-3-(4-methylphenyl)acrylic acid which melted at 210°-215° C. in a yield of 560 g. This compound (320 g) and thionyl chloride (252 g) were dissolved in acetonitrile (200 ml) by heating for 1 hour. After the reaction, acetonitrile and thionyl chloride were distilled off under a reduced pressure, and the resulting solid was added to a solution composed of hydroxyethyl methacrylate (244.8 g), pyridine (149 g) and acetonitrile (2 liters). The reaction was carried out for 2 hours while keeping the reaction temperature at 40° C. or less. After the reaction, the reaction solution was poured in iced water to separate crystals. The resulting crystals were recrystallized from ethyl alcohol (3 liters) to obtain 360 g of the desired product which melted at 74°-75° C.

Workup

  1. concentrationwas concentrated to 600 ml under a reduced pressure, and it
  2. additionwas poured in 1 liter of iced water
  3. customto separate crystals
  4. filtrationThe separated crystals were filtered out by suction

Sources & evidence

ORD record
ord-a807c31528e34848917106456c526521
Source dataset
uspto-grants-1987_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04645735

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes