Hydrochloric Acid → Butanoic acid, 4-chloro-, 1,1-dimethylethyl ester

4-Chlorobutyryl chloride (14.1 g) was added dropwise with stirring under ice-cooling to a mixture of tert-butanol (18.5 g) and dimethylaniline (18.2 g). The resulting mixture was stirred for 2 hours in an oil bath (100° C.). Ether (200 ml), water (100 ml) and 1N hydrochloric acid (50 ml) were added to the reaction mixture and mixed with shaking. The organic layer was washed successively with 1N hydrochloric acid, an aqueous sodium bicarbonate and brine and dried over anhydrous magnesium sulfate. The solvent was distilled off and then the residue was subjected to distillation under reduced pressure to obtain tert-butyl 4-chlorobutyrate (13.2 g).

1. stirringThe resulting mixture was stirred for 2 hours in an oil bath (100° C.)
2. additionmixed
3. stirringwith shaking
4. washThe organic layer was washed successively with 1N hydrochloric acid
5. dry with materialan aqueous sodium bicarbonate and brine and dried over anhydrous magnesium sulfate
6. distillationThe solvent was distilled off
7. distillationthe residue was subjected to distillation under reduced pressure

ORD record

ord-bb3590d90fe24b59b39da3351c282055

Source dataset

uspto-grants-1996_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05532171