Hydrochloric Acid → HCID 86731380, compound

A mixture of cyclopropylmethyl 4-(cyclopropylmethoxy)-2,6-dimethylbenzoate (1.35 g), THF (15 mL), methanol (15 mL) and 1M sodium hydroxide (15 mL) was stirred at room temperature for 2 hr, and then at 70° C. for 2 hr. To the reaction mixture was added 4M lithium hydroxide (10 mL), and the obtained mixture was stirred overnight at 70° C., and then at 100° C. for 2 hr. To the reaction mixture was added 2-ethoxyethanol (10 mL), and the obtained mixture was stirred at 120° C. for 2 days. The reaction mixture was cooled to 0° C., and acidified with 6M hydrochloric acid, and the mixture was extracted with ethyl acetate. The combined organic layer were washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (960 mg).

1. waitat 70° C. for 2 hr
2. stirringthe obtained mixture was stirred overnight at 70° C.
3. waitat 100° C. for 2 hr
4. stirringthe obtained mixture was stirred at 120° C. for 2 days
5. temperatureThe reaction mixture was cooled to 0° C.
6. extractionthe mixture was extracted with ethyl acetate
7. washThe combined organic layer were washed with saturated brine
8. dry with materialdried over anhydrous magnesium sulfate
9. customthe solvent was evaporated under reduced pressure
10. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

ORD record

ord-daecf1b190db4448a6af8ede675adf0c

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133129B2