Methanol → Methyl 3-Hydroxyphenylacetate

A catalytic quantity of concentrated sulphuric add (1.0 ml) was added to a solution of (3-hydroxy)phenylacetic acid (17.38 g, 0.114tool) in methanol (100 ml). The reaction mixture was stirred for 3 hours at room temperature and then concentrated in vacuo. The residue was partitioned between diethyl ether (200 ml) and a saturated aqueous solution of sodium hydrogen carbonate (200 ml). The ether phase was separated and washed with non-saturated sodium hydrogen carbonate solution (200 ml) and saturated brine solution (100 ml). The ether extract was dried over magnesium sulphate. The solvent was evaporated and the residue dried to afford methyl 3-hydroxyphenylacetate as an amber oil (18.61 g, 98%); δH (360 MHz, CDCl3) 3.58 (2H, s, CH2), 3.70 (3H, s, COOCH3), 5.54 (1H, br s, OH), 6.74 (2H, m, ArH), 6.81 (1H, d, J 8 Hz, ArH), 7.17 (1H, t, J 8 Hz, ArH).

1. additionA catalytic quantity of concentrated sulphuric add (1.0 ml)
2. concentrationconcentrated in vacuo
3. customThe residue was partitioned between diethyl ether (200 ml)
4. customThe ether phase was separated
5. washwashed with non-saturated sodium hydrogen carbonate solution (200 ml) and saturated brine solution (100 ml)
6. extractionThe ether extract
7. dry with materialwas dried over magnesium sulphate
8. customThe solvent was evaporated
9. customthe residue dried

ORD record

ord-a964a72cb35a4fa5a6fcfb1307d92e3c

Source dataset

uspto-grants-1994_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05348962