3-Chloro-4'-methoxypropiophenone → 4-Acryloylphenol

2-Chloroethyl 4-methoxyphenyl ketone (b) (69.4 g) was dissolved in methylene chloride (200 mL), to which was added aluminium chloride (130.8 g) little by little. The resulting mixture was heated with a mantle heater for 2 hours under reflux. After the reaction, the reaction liquid was cooled and poured into ice, and the organic phase was extracted out with ethyl acetate (200 mL) and transferred into a separating funnel. The organic phase was washed with water, and then processed with aqueous 2 M NaOH solution to extract out the intended product into the solution. The aqueous alkali solution was acidified with 6 M hydrochloric acid, and then again extracted with ethyl acetate. The solvent was evaporated away under reduced pressure, and the residue was recrystallized from toluene to obtain 37.9 g of colorless crystals, 4-hydroxyphenyl vinyl ketone (c).

1. temperatureThe resulting mixture was heated with a mantle heater for 2 hours
2. temperatureunder reflux
3. customAfter the reaction
4. customthe reaction liquid
5. temperaturewas cooled
6. additionpoured into ice
7. extractionthe organic phase was extracted out with ethyl acetate (200 mL)
8. customtransferred into a separating funnel
9. washThe organic phase was washed with water
10. extractionto extract out the intended product into the solution
11. extractionagain extracted with ethyl acetate
12. customThe solvent was evaporated away under reduced pressure
13. customthe residue was recrystallized from toluene

ORD record

ord-fefbbb28bde14f2ea033f0481f128fb4

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07357964B2