Benzyl Alcohol → Benzyl 2-cyanoacetate

HRID 229493ノート

反応式

HRID 229493 の反応式
[C:1]([CH2:3][C:4]([OH:6])=[O:5])#[N:2].[CH2:7](O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:7]([O:5][C:4](=[O:6])[CH2:3][C:1]#[N:2])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

参加物

5

反応物 3

HCID 244Benzyl AlcoholHCID 6101p-Toluenesulfonic acidHCID 9740Cyanoacetic acid

生成物 1

HCID 560818Benzyl 2-cyanoacetate

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a mixture of cyanoacetic acid (VII) 2.34 g (27.5 mmol) and benzyl alcohol (VIIIa) 2.70 g (25 mmol) in 60 mL of toluene 50 mg of p-TsOH was added and the mixture was refluxed in a flask with a Dean-Stark trap for 24 h. The mixture was cooled down and toluene was washed with H2O and toluene was evaporated. The residue was distilled in vacuo (Kugelrohr apparatus, 0.1 mm Hg, T. oven 170-180° C.). Yield 3.36 g (77%), a colorless oil. MS (m/z, rel. intensity, %): 167.0 ([M+NH4−CN]+, 27), 193.0 ([M+NH4]+, 100).

後処理

  1. additionwas added
  2. temperaturethe mixture was refluxed in a flask with a Dean-Stark trap for 24 h
  3. temperatureThe mixture was cooled down
  4. washtoluene was washed with H2O and toluene
  5. customwas evaporated
  6. distillationThe residue was distilled in vacuo (Kugelrohr apparatus, 0.1 mm Hg, T. oven 170-180° C.)

出典と根拠

ORDレコード
ord-e39c70ae93a8455da1ace198e8eb0052
出典データセット
uspto-grants-2009_07
特許番号
US07563820B2

反応ノート

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