Ammonium Chloride → HCID 59133005, compound

Temperature

-7.5 °C

263.4 g of methoxymethyl triphenylphosphonium chloride was dispersed in 750 mL of tetrahydrofuran, to which 86.2 g of potassium-t-butoxide was added at −9 to −4° C. for 5 minutes. The solution was further stirred at −4 to −11° C. for 30 minutes. Then, 100.0 g of methyl 4-oxocyclohexane-carboxylate was dissolved in 300 mL of THF, which was added dropwise to the above solution at −10 to 4° C. for 80 minutes. The solution was further stirred at 0 to 4° C. for 60 minutes, and then 7.0 g of ammonium chloride and 20 mL of water were added thereto. The solvent of the reaction mixture was evaporated under reduced pressure. Then, 600 mL of hexane was added and the solution was stirred under room temperature for 30 minutes. The precipitate was filtered off. Then, the precipitate was again suspended and washed with 600 mL of hexane, combined with the hexane filtrate, and washed with a mixed solution of methanol-water (1:1), water, and saturated saline in this order. The resultant product was dried over anhydrous sodium sulfate. Then, the solvent was evaporated under reduced pressure, to obtain 103 g of methyl 4-methoxymethylidene-cyclohexane-carboxylate in the form of an oil-like product.

1. additionwas added at −9 to −4° C. for 5 minutes
2. additionwhich was added dropwise to the above solution at −10 to 4° C. for 80 minutes
3. stirringThe solution was further stirred at 0 to 4° C. for 60 minutes
4. customThe solvent of the reaction mixture was evaporated under reduced pressure
5. additionThen, 600 mL of hexane was added
6. stirringthe solution was stirred under room temperature for 30 minutes
7. filtrationThe precipitate was filtered off
8. washwashed with 600 mL of hexane
9. washwashed with a mixed solution of methanol-water (1:1), water, and saturated saline in this order
10. dry with materialThe resultant product was dried over anhydrous sodium sulfate
11. customThen, the solvent was evaporated under reduced pressure

ORD record

ord-57798d6e9a80474fb435dfbeca16ac06

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07651630B2