Water → 2-Chloro-6-phenoxybenzenemethanol

HRID 1956593ノート

反応式

HRID 1956593 の反応式
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:3]=1[CH:4]=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:3]=1[CH2:4][OH:5]

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 186636022-Chloro-6-phenoxybenzaldehydeHCID 21226445Aluminium lithium hydride

生成物 1

HCID 223783762-Chloro-6-phenoxybenzenemethanol収率 94%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

19.0 g (77.67 mmol) of 2-chloro-6-phenoxy-benzaldehyde in approximately 40 ml of tetrahydrofuran are added dropwise at room temperature in the course of 30 minutes to a suspension of 4.42 g (116.5 mmol) of lithium aluminium hydride in approximately 150 ml of tetrahydrofuran. The mixture is then heated under reflux for 4 hours, cooled and hydrolysed with 4.4 ml of water, 4.4 ml of 4N sodium hydroxide and 13.2 ml of water. The reaction mixture is boiled under reflux for 30 minutes, cooled and filtered, and the suction filter residue is 3× taken up in ethyl acetate, boiled under reflux for 15 minutes and filtered. The combined filtrates are concentrated. 17.97 g (76.57 mmol)=94% of crude (2-chloro-6-phenoxy-phenyl)-methanol are obtained in the form of a yellow oil; TLC (silica gel; ethyl acetate/hexane=1:1; UV): Rf =0.68; 1H-NMR (CDCl3, 200 MHz): 4.90 (s, 2H); 6.76-7.40 (m, 8H).

後処理

  1. temperatureThe mixture is then heated
  2. temperatureunder reflux for 4 hours
  3. temperatureunder reflux for 30 minutes
  4. temperaturecooled
  5. filtrationfiltered
  6. filtrationthe suction filter residue
  7. temperatureunder reflux for 15 minutes
  8. filtrationfiltered
  9. concentrationThe combined filtrates are concentrated

出典と根拠

ORDレコード
ord-090b2c4b263b4e7285e3c7e5b836cb3d
出典データセット
uspto-grants-1998_07
特許番号
US05780501

反応ノート

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