Ammonium Hydroxide → HCID 51358271, compound

(Methoxymethyl) triphenylphosphonium chloride (12.5 g, 36.5 mmol) was dissolved in THF (80 mL), and tBuOK (4.10 g, 36.5 mmol) and methyl 4-formylbenzoate (3.0 g, 18.3 mmol) dissolved in THF (20 mL) were added thereto while cooling with ice, followed by stirring at room temperature for 16 hours. Water was added to the resulting mixture, and after extraction with ethyl acetate, the residue was purified using medium pressure flash column chromatography (silica gel; ethyl acetate:hexane=1:8), thereby giving a mixture of (E)- and (Z)-methyl 4-(2-methoxyvinyl)benzoate (2.98 g) as an oil. The obtained mixture was dissolved in a mixture of dioxane (60 mL) and water (60 mL), and N-bromosuccinimide (3.04 g, 17.1 mmol) was added thereto at −10° C., followed by stirring for 5 minutes, and further stirring at room temperature for 1 hour. Thiourea (1.18 g, 15.5 mmol) was added to the mixture, followed by stirring at 80° C. for 1.5 hours. Ammonia aqueous solution (6 mL) was added to the resulting mixture to stop the reaction, and after stirring for 1 hour, the precipitate was collected by filtration, thereby giving the title compound (2.80 g, 65% for 2 steps) as a white solid.

1. additionwere added
2. temperaturewhile cooling with ice
3. extractionafter extraction with ethyl acetate
4. customthe residue was purified
5. customgiving
6. additionwas added
7. customat −10° C.
8. stirringby stirring for 5 minutes
9. stirringfurther stirring at room temperature for 1 hour
10. stirringby stirring at 80° C. for 1.5 hours
11. customthe reaction
12. stirringafter stirring for 1 hour
13. filtrationthe precipitate was collected by filtration

ORD record

ord-3c9f3f5437f74f34b22bce0ebd963633

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181183B2