Benzoic acid, 2,3-dichloro-, methyl ester → 2,3-Dichlorobenzyl alcohol

Temperature

0 °C

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).

1. stirringThen the mixture was stirred at room temperature for 2 h
2. customThe reaction mixture was quenched with ethyl acetate (15 mL), water (7.5 mL), 15% NaOH (7.5 mL) and water (22.5 mL)
3. filtrationfiltered
4. concentrationthe filtrate was concentrated
5. dissolutionThe resulting residue was dissolved with DCM (500 mL)
6. washwashed with brine
7. dry with materialThe organic layer was dried over Na2SO4
8. filtrationfiltered
9. concentrationthe filtrate was concentrated

ORD record

ord-06ed947d354945b5b89204d859be8b30

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09096605B2