Methanol → Methyl 3-Hydroxyphenylacetate

To a solution of 3-hydroxyphenyl acetic acid, (5.0 g, 0.033 mol) in methanol (100 mL) was added concentrated sulfuric acid (1 mL) and the reaction mixture stirred at room temperature for 12 hours. After concentration to remove methanol, the crude oil was dissolved in ethyl acetate (75 mL), washed with water (50 ml), saturated aqueous NaHCO3 (50 mL), and brine (50 ml). The organic layer was dried over Na2SO4, and concentrated to give the methyl ester (1) as an oil (5.28 g) in 96% yield, which was used without further purification. 1H NMR (CDCl3) δ 7.17 (t, 1H), 6.81 (m, 3H), 6.48 (s, 1H), 3.69 (s, 3H), 3.57 (s, 2H). 13C NMR (CDCl3) δ 169.9, 153.3, 132.3, 126.9, 118.4, 111.5, 57.8, 38.4.

1. concentrationAfter concentration
2. customto remove methanol
3. dissolutionthe crude oil was dissolved in ethyl acetate (75 mL)
4. washwashed with water (50 ml), saturated aqueous NaHCO3 (50 mL), and brine (50 ml)
5. dry with materialThe organic layer was dried over Na2SO4
6. concentrationconcentrated

ORD record

ord-23e08e783aa449929d4603d228d19840

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08993628B2