N-Methylbenzanilide → Benzyl Alcohol

HRID 1472978ノート

反応式

HRID 1472978 の反応式
[CH3:1][N:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>ClCCl>[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:1][NH:2][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

参加物

4

反応物 1

HCID 74736N-Methylbenzanilide

生成物 2

HCID 244Benzyl Alcohol収率 90%HCID 7515N-Methylaniline収率 82%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
100 °C

実験手順

0.01 mmol of the complex 1 produced in Example 1 and 5 mmol of N-methyl-N-phenylbenzamide were placed in a 50 mL-autoclave equipped with a stirrer, and the autoclave was purged with nitrogen. 1.5 mL of Methanol and 2.5 mL of methanol solution of 2.0 M sodium methoxide were added to the autoclave, and the autoclave was purged with hydrogen. The resulting mixture was stirred under hydrogen atmosphere (5 MPa) and 100 degrees C. for 16 hours to obtain a reaction solution. After the completion of reaction, the reaction solution was cooled, diluted with 40 mL of dichloromethane, and subjected to silica gel filtration (eluting solvent: dichloromethane/methanol=10/1). The thus obtained solution was concentrated, and then the resulting residue was purified by silica gel column chromatography (silica gel: 40 g, hexane/ethyl acetate=8/1 to 4/1). As a result, benzyl alcohol (425 mg, 90%) and N-methyl-N-phenylamine (440 mg, 82%) were obtained.

後処理

  1. customequipped with a stirrer
  2. customthe autoclave was purged with nitrogen
  3. addition1.5 mL of Methanol and 2.5 mL of methanol solution of 2.0 M sodium methoxide were added to the autoclave
  4. customthe autoclave was purged with hydrogen
  5. customfor 16 hours to obtain a reaction solution
  6. customAfter the completion of reaction
  7. temperaturethe reaction solution was cooled
  8. filtrationsubjected to silica gel filtration (eluting solvent: dichloromethane/methanol=10/1)
  9. concentrationThe thus obtained solution was concentrated
  10. customthe resulting residue was purified by silica gel column chromatography (silica gel: 40 g, hexane/ethyl acetate=8/1 to 4/1)

出典と根拠

ORDレコード
ord-e72a6bf55aea41858d4bca1ac253f816
出典データセット
uspto-grants-2015_04
特許番号
US09012690B2

反応ノート

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