4-Chloro-3-methoxybenzoic acid → (4-Chloro-3-methoxyphenyl)methanol
Reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[O:11][CH3:12].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[O:11][CH3:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 4-chloro-3-methoxybenzoic acid (1.12 g, 5.98 mmol) in THF (30 mL) was stirred on an ice bath and treated with a 1.0 M tetrahydrofuran solution of lithium aluminum hydride (7.18 mL, 7.18 mmol) over about a 5 min. period. The solution was stirred on ice for 2 h, and then quenched with rapid stirring by the slow dropwise addition of water (0.27 mL), followed by 15% aqueous sodium hydroxide (0.27 mL), then water (0.82 mL) again. Upon completion of addition, the resulting suspension was filtered and the collected solid was washed with ethyl acetate. The filtrate was concentrated under vacuum to provide (4-chloro-3-methoxyphenyl)methanol as a colorless oil (737 mg, 71%). 1H NMR (400 MHz, CDCl3) δ ppm 3.92 (s, 3 H) 4.67 (s, 2 H) 6.87 (d, J=7.6 Hz, 1 H) 6.98 (s, 1 H) 7.33 (d, J=7.6 Hz, 1 H).