3-Methoxybenzaldehyde → Methyl (3-methoxystyryl) ether

Ninety grams of m-anisaldehyde, 250 g of (methoxymethyl)triphenylphosphonium chloride and 800 ml of tetrahydrofuran were mixed, and then 82.5 g of potassium tert-butoxide was added to this mixed suspension under ice-cooling, and the solution was stirred for 2 hours at room temperature. The reaction solution was poured in ice water, and after distilling out the THF, the mixture was extracted with ethyl acetate. The extract solution was washed with sodium bicarbonate aqueous solution and dried. The extract solution was concentrated to obtain a residue to which hexane was then added, and the resulting precipitate was filtered out. The filtrate was then concentrated, and the residue was subjected to silica gel column chromatography. Elution was then performed with a mixed solvent of hexane:ethyl acetate=20:1, to obtain 90 g of methyl (3-methoxystyryl) ether.

1. temperaturecooling
2. distillationafter distilling out the THF
3. extractionthe mixture was extracted with ethyl acetate
4. washThe extract solution was washed with sodium bicarbonate aqueous solution
5. customdried
6. concentrationThe extract solution was concentrated
7. customto obtain a residue to which hexane
8. additionwas then added
9. filtrationthe resulting precipitate was filtered out
10. concentrationThe filtrate was then concentrated
11. washElution

ORD record

ord-a6cd1924f0c44ce2b51796fe147bdfb6

Source dataset

uspto-grants-1997_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05677326