Methanol → Methyl 4-chloro-2-hydroxybenzoate

4-Chlorosalicylic acid (34.51 g, 0.2 mol) (Aldrich) was suspended in a solution of methanol (100 mL) and concentrated sulfuric acid (8 mL). The mixture was heated at reflux for 17 h. After cooling to room temperature, the mixture was concentrated under reduced pressure. The resulting residue was dissolved in ether (400 mL) and washed successively with water (400 mL), saturated aqueous sodium bicarbonate (400 mL), and saturated aqueous sodium chloride (400 mL). The ether solution was then dried (MgSO4), filtered, and concentrated. The resulting yellow oil was distilled to give methyl 4-chlorosalicylate. (Yield 32.89 g, 88%; b.p. 86-90° C., 0.15 mm Hg).

1. temperatureThe mixture was heated
2. temperatureat reflux for 17 h
3. concentrationthe mixture was concentrated under reduced pressure
4. dissolutionThe resulting residue was dissolved in ether (400 mL)
5. washwashed successively with water (400 mL), saturated aqueous sodium bicarbonate (400 mL), and saturated aqueous sodium chloride (400 mL)
6. dry with materialThe ether solution was then dried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated
9. distillationThe resulting yellow oil was distilled

ORD record

ord-bc7ce5f58fe649bdb7b0418a62868a7a

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06313310B1