Hydrochloric Acid → HCID 12681390, compound

Temperature

80 °C

Malonic acid (93.74 g, 0.90 mol), acetonitrile (306 mL), morpholine (26 mL, 0.30 mol), and pyridine (97 mL, 1.20 mol) were added in this order to the solution of 2-ethylpent-4-enal (58.44 g) in toluene obtained by the method described above under a nitrogen atmosphere, and the mixture was slowly warmed to approximately 80° C. over approximately 1 hour. After stirring at approximately 80° C. for 13.5 hours, malonic acid (6.24 g, 0.06 mol) was added thereto, and the mixture was further stirred at approximately 80° C. for 3 hours and cooled to room temperature. To the reaction mixture, water (408 mL) was added, and concentrated hydrochloric acid (130 mL) was added to separate an organic layer. The aqueous layer was subjected to extraction with toluene (153 mL), and the extract was combined with the organic layer, followed by two extractions of the compound of interest into aqueous layers using a 2 M aqueous NaOH solution (360 mL×1 and 90 mL×1). The aqueous layers were combined and then adjusted to be acidic by the addition of concentrated hydrochloric acid (80 mL), followed by two extractions with toluene (each with 204 mL). The organic layers were combined and then washed with water (102 mL). The organic layer was concentrated under reduced pressure to obtain the title compound (100.57 g, yellow oil substance).

1. customobtained by the method
2. stirringthe mixture was further stirred at approximately 80° C. for 3 hours
3. temperaturecooled to room temperature
4. customto separate an organic layer
5. extractionThe aqueous layer was subjected to extraction with toluene (153 mL)
6. extractionfollowed by two extractions of the compound of interest into aqueous layers
7. additionto be acidic by the addition of concentrated hydrochloric acid (80 mL)
8. extractionfollowed by two extractions with toluene (each with 204 mL)
9. washwashed with water (102 mL)
10. concentrationThe organic layer was concentrated under reduced pressure

ORD record

ord-a6b48c20116040bf9a9ae014f66c03f8

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09162971B2