Methanol → Methyl 3-Hydroxyphenylacetate

Temperature

70 °C

3-hydroxyphenylacetic acid (111 g, 735.84 mmol) was dissolved under argon in 1000 ml methanol and then sulfuric acid (31.5 mL, 588.6 mmol) was added. The brown mixture was heated (70° C.) for 3 hours, at this temperature, and then cooled to room temperature. The mixture was concentrated in a rotary evaporator and then cooled down to 0° C. 250 mL water and 70 g of NaHCO3 were added with stirring, until the pH was approximately 7.250 mL water was added and 500 ml of ethyl acetate was added. Stirring was pursued for 20 minutes. The organic phase was separated and the aqueous layer extracted with 250 mL ethyl acetate. Drying over magnesium sulfate and concentration in a rotatory evaporator left a brownish oil (118 g, 97%) that was dried at the pump. MS: m/e=165 (M−H+).

1. temperatureat this temperature, and then cooled to room temperature
2. concentrationThe mixture was concentrated in a rotary evaporator
3. temperaturecooled down to 0° C
4. addition250 mL water and 70 g of NaHCO3 were added
5. additionwas added
6. addition500 ml of ethyl acetate was added
7. stirringStirring
8. customThe organic phase was separated
9. extractionthe aqueous layer extracted with 250 mL ethyl acetate
10. dry with materialDrying over magnesium sulfate and concentration in a rotatory evaporator
11. waitleft a brownish oil (118 g, 97%) that
12. customwas dried at the pump

ORD record

ord-936a19a3148c4046961f46bfb4a7f565

Source dataset

uspto-grants-2004_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06818774B2