3,5-Dichlorobenzoyl chloride → 3,5-Dichlorobenzylic alcohol

To a stirred solution of 3,5-dichlorobenzoyl chloride (712 mg, 3.40 mmole) in THF (6 ml) at 0° C. is added dropwise a solution of sodium borohydride (227 mg, 6.0 mmole), in N-methyl pyrrolidinone (1.5 ml) maintaining the temperature at ≤18° C. The reaction mixture is stirred for 2 hours at ambient temperature and then partitioned with 0.5 N aqueous HCl (60 ml) and EtOAc (60 ml). The layers are separated and the aqueous layer is washed with EtOAc (20 ml). The combined organic layer is washed with H2O (60 ml) and brine (40 ml), dried (Na2SO4), filtered, and concentrated to give crude product as a crystalline solid. One recrystallization from hot cyclohexane (7.5 ml) gives 2, i.e., 3,5-dichlorobenzyl alcohol (451 mg, 2.55 mmole, 75%, m.p. 77°-77.5° C.).

1. custompartitioned with 0.5 N aqueous HCl (60 ml) and EtOAc (60 ml)
2. customThe layers are separated
3. washthe aqueous layer is washed with EtOAc (20 ml)
4. washThe combined organic layer is washed with H2O (60 ml) and brine (40 ml)
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated
8. customto give crude product as a crystalline solid
9. customOne recrystallization from hot cyclohexane (7.5 ml)

ORD record

ord-d6658045fc00426d9de7fea38c6e92d2

Source dataset

uspto-grants-1989_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04847257