Hydrochloric Acid → HCID 73554943, compound

The crude 1,3-dimethyl 2-(3,5-dichlorophenyl)propanedioate form Step A was taken up in methanol (150 mL) and water (300 mL). To this mixture was added 50% aqueous sodium hydroxide (120 g, 1.5 mol) over 30 min at room temperature. The reaction mixture was stirred at room temperature for 18 hours and then cooled to 10° C. in an ice bath. The mixture was acidified with concentrated hydrochloric acid (135 mL of 37%) over 30 min while maintaining the temperature of the reaction mixture at less than 17° C. The reaction mixture was extracted with ethyl acetate (600 mL) and the organic phase was concentrated under vacuum to give a viscous oil. The crude oil was treated with dichloromethane (200 mL) and stirred till a thick slurry formed. The slurry was filtered and dried via suction filtration under a nitrogen blanket for 48 hours at room temperature to give a solid (76.0 g, 84% over 2 steps).

1. temperaturecooled to 10° C. in an ice bath
2. temperaturewhile maintaining the temperature of the reaction mixture at less than 17° C
3. extractionThe reaction mixture was extracted with ethyl acetate (600 mL)
4. concentrationthe organic phase was concentrated under vacuum
5. customto give a viscous oil
6. stirringstirred till a thick slurry
7. customformed
8. filtrationThe slurry was filtered
9. customdried via suction filtration under a nitrogen blanket for 48 hours at room temperature
10. customto give a solid (76.0 g, 84% over 2 steps)

ORD record

ord-1294050c030848afaad49fbc2584b7e0

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09238650B2