Hydrochloric Acid → 3-Chloromandelic acid

A mixture of 158 g of 3-chlorobenzaldehyde, 111.6 g of trimethylsilylnitrile and a catalytic amount of zinc iodide was heated at 90° C. for 2 hours, with stirring. The reaction mixture was ice-cooled, and 350 ml of concentrated aqueous hydrochloric acid were added to it. The resulting mixture was then heated under reflux for 1 hour, after which it was mixed with water and with ethyl acetate. The ethyl acetate layer was separated and mixed with a 30% w/v aqueous solution of sodium hydroxide. The aqueous layer was separated, washed three times with ethyl acetate and then acidified with concentrated aqueous hydrochloric acid, after which it was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, to give the title compound as crystals, melting at 110°-114° C.

1. temperaturecooled
2. temperatureThe resulting mixture was then heated
3. temperatureunder reflux for 1 hour
4. customThe ethyl acetate layer was separated
5. additionmixed with a 30% w/v aqueous solution of sodium hydroxide
6. customThe aqueous layer was separated
7. washwashed three times with ethyl acetate
8. extractionafter which it was extracted with ethyl acetate
9. washThe extract was washed with water
10. dry with materialdried over anhydrous sodium sulfate
11. customThe solvent was then removed by distillation under reduced pressure

ORD record

ord-d7a726eb470f4e368e9d6db210013873

Source dataset

uspto-grants-1996_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05576340