Water → 2-Chloro-6-phenoxybenzenemethanol

HRID 1956593노트

반응식

HRID 1956593 반응식
[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]

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 186636022-Chloro-6-phenoxybenzaldehydeHCID 21226445Aluminium lithium hydride

생성물 1

HCID 223783762-Chloro-6-phenoxybenzenemethanol수율 94%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-090b2c4b263b4e7285e3c7e5b836cb3d
출처 데이터셋
uspto-grants-1998_07
특허 번호
US05780501

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