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

HRID 1026621ノート

反応式

HRID 1026621 の反応式
[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]

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-dbd9923988d24681bb3fe0c241e318cb
出典データセット
uspto-grants-2014_05
特許番号
US08729274B2

反応ノート

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