Water → 2-Chloro-6-phenoxybenzenemethanol
Reaction equation
[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]Participants
Procedure
19.0 g (77.67 mmol) of 2-chloro-6-phenoxybenzaldehyde 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).
Workup
- temperatureThe mixture is then heated
- temperatureunder reflux for 4 hours
- temperatureunder reflux for 30 minutes
- temperaturecooled
- filtrationfiltered
- filtrationthe suction filter residue
- temperatureunder reflux for 15 minutes
- filtrationfiltered
- concentrationThe combined filtrates are concentrated
Sources & evidence
- ORD record
- ord-d332945993db4d0b81ad63a03c8afc08
- Source dataset
- uspto-grants-1998_07
- Patent number
- US05780500
Reaction notes
Loading…