Diazomethane → Methyl 3-(2-hydroxyphenyl)prop-2-enoate

To a stirred mixture of ortho-hydroxycinnamic acid (1.00 g, 6.09 mmol) in 10 mL of ether and 10 mL of methanol was added etheral diazomethane until the mixture became yellowish. The mixture was stirred at room temperature for 15 minutes, and the excess diazomethane was destroyed with the addition of acetic acid. The mixture was concentrated in vacuo and diluted with 100 mL of ethyl acetate. This ethyl acetate solution was washed with saturated sodium bicarbonate solution (3×60 mL) and brine (1×60 mL). The organic layer was dried (magnesium sulfate), filtered and concentrated in vacuo to give 1.02 g (94%) of methyl ortho-hydroxycinnamate B.

1. customthe excess diazomethane was destroyed with the addition of acetic acid
2. concentrationThe mixture was concentrated in vacuo
3. additiondiluted with 100 mL of ethyl acetate
4. washThis ethyl acetate solution was washed with saturated sodium bicarbonate solution (3×60 mL) and brine (1×60 mL)
5. dry with materialThe organic layer was dried (magnesium sulfate)
6. filtrationfiltered
7. concentrationconcentrated in vacuo

ORD record

ord-23b92547efaf40508d4faeeb594ee43e

Source dataset

uspto-grants-1998_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05827868