Benzoic acid, 2,3-dichloro-, methyl ester → (2,3-Dichlorophenyl)methanol
Reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:9]=1[C:10](OC)=[O:11]>C1COCC1>[Cl:7][C:8]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:9]=1[CH2:10][OH:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A suspension of LiAlH4 (7.4 g, 0.195 mol) in THF (500 mL) was stirred at 0° C. A solution of methyl 2,3-dichlorobenzoate (49 g, 0.244 mol) in THF (50 mL) was added dropwise into the above mixture at 0-5° C. Then the mixture was stirred at room temperature for 2 h. The reaction mixture was quenched with ethyl acetate (15 mL), water (7.5 mL), 15% NaOH (7.5 mL) and water (22.5 mL), filtered and the filtrate was concentrated. The resulting residue was dissolved with DCM (500 mL) and washed with brine. The organic layer was dried over Na2SO4, filtered and the filtrate was concentrated to provide the titled compound (37 g, 88%), as a white solid; 1H NMR (300 MHz, CDCl3) δ ppm 4.81 (d, J=6.3 Hz, 2H), 7.24 (t, J=7.8 Hz, 1H), 7.42-7.45 (m, 2H).