Water → 2-Cyano-3-(2,6-dichlorophenyl)acrylic acid

HRID 1026621Notes

Reaction equation

HRID 1026621 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]=O.[C:11]([CH2:13][C:14]([OH:16])=[O:15])#[N:12].C([O-])(=O)C.[NH4+].N1C=CC=CC=1.O>C1(C)C=CC=CC=1>[C:11]([C:13](=[CH:4][C:3]1[C:2]([Cl:1])=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:10])[C:14]([OH:16])=[O:15])#[N:12]

Participants

7

Reactant 5

HCID 962WaterHCID 1049PyridineHCID 67372,6-DichlorobenzaldehydeHCID 9740Cyanoacetic acidHCID 517165Ammonium Acetate

Product 1

HCID 545137902-Cyano-3-(2,6-dichlorophenyl)acrylic acidYield 4.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred mixture of 2,6-dichlorobenzaldehyde (609 mmol, 106.5 g), cyanoacetic acid (609 mmol, 51.8 g), ammonium acetate (122 mmol, 9.38 g), pyridine (1065 mmol, 86 ml, 84 g) and toluene (468 ml) was stirred at reflux using a Dean-Stark apparatus until one equivalent of water was collected (NB Oil bath temperature should not exceed 120° C. to avoid decarboxylation at this stage—lag Dean-Stark well). The reaction mixture was allowed to cool and the solid precipitate filtered and stirred with 10% aqueous HCl. The solid was again collected by filtering to afford pure 2-cyano-3-(2,6-dichlorophenyl)acrylic acid (7.21 g). The filtrate was concentrated in vacuo to give the crude 2-cyano-3-(2,6-dichlorophenyl)acrylic acid (˜135 g). Recrystallisation from toluene afforded pure 2-cyano-3-(2,6-dichlorophenyl)acrylic acid (101 g).

Workup

  1. temperatureat reflux
  2. customwas collected (NB Oil bath temperature should not
  3. customexceed 120° C.
  4. temperatureto cool
  5. filtrationthe solid precipitate filtered
  6. stirringstirred with 10% aqueous HCl
  7. customThe solid was again collected
  8. filtrationby filtering

Sources & evidence

ORD record
ord-dbd9923988d24681bb3fe0c241e318cb
Source dataset
uspto-grants-2014_05
Patent number
US08729274B2

Reaction notes

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