Citric Acid → 2-(Cyanomethyl)-5-methylbenzoic acid

HRID 1783297ノート

反応式

HRID 1783297 の反応式
[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[N:12]O)[C:8]2=[O:11])=[CH:4][CH:3]=1.[OH-].[Na+].C1(C)C=CC(S(Cl)(=O)=[O:23])=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O>[C:7]([CH2:6][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:10][C:9]=1[C:8]([OH:11])=[O:23])#[N:12]

参加物

6

反応物 4

HCID 311Citric AcidHCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 587173366-Methyl-2-hydroxyimino-1-indanone

生成物 1

HCID 230848102-(Cyanomethyl)-5-methylbenzoic acid収率 44.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

6-Methyl-2-hydroxyimino-1-indanone (37 g) and sodium hydroxide (19.7 g) were dissolved in water (287 mL), and p-toluenesulfonyl chloride (44.3 g) was added with stirring at 50° C. After the completion of the reaction, aqueous citric acid solution was added to acidify the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated. Ether was added to the precipitated crystals, and the crystals were collected by filtration to give 2-cyanomethyl-5-methylbenzoic acid (16.3 g).

後処理

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated
  6. additionEther was added to the precipitated crystals
  7. filtrationthe crystals were collected by filtration

出典と根拠

ORDレコード
ord-8d701be4f7e5458e98f5a8f5e6b675b1
出典データセット
uspto-grants-2009_03
特許番号
US07501412B2

反応ノート

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