2-CHLORO-4-HYDROXY-BENZOIC ACID METHYL ESTER

Tan crystalline powder

SOCl2 (1.5 ml) was added to 2-chloro-4-hydroxy-benzoic acid (5 g, 0.03 mmol) in methanol (10 ml). The mixturewas slowly warmed from room temperature to reflux temperature and the reaction solution was refluxed for 12 hoursand concentrated under reduced pressure to give compound 132A (red solid, 5.4 g, the yield was 100percent).1H NMR (400MHz, DMSO-d6) δ: 10.71 (s, 1H), 7.84 - 7.71 (m, 1H), 6.91 (d, J=2.4 Hz, 1H), 6.82 (dd, J=2.4, 8.7 Hz, 1H), 3.79 (s, 3H).A solution of 2-chloro-4-hydroxybenzoic acid (4.20 g) and concentrated sulfuric acid (2.5 mL) in methanol (50 mL) was heated under reflux for three days. The reaction mixture was neutralized with a saturated sodium hydrogen carbonate aqueous solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate and concentrated and dried under reduced pressure, and 4.18 g (92percent) of the title compound was obtained as a brown solid.To a solution of 2-chloro-4-hydroxybenzoic acid (200.0 mg, 1.16 mmol) in methanol (5 mL) was added thionyl chloride (413.6 mg, 3.48 mmol) dropwise at 0 °C. The reaction mixture was stirred at 70 °C for 2 h and concentrated. The residue was diluted withwater (15 mL) and extracted with EtOAc (l5mL x 2). The organic layers were combined and washed with water (30 mL x 2) and brine (20 mL). The organic layers were separated, dried over Na2504 and concentrated to obtain methyl 2-chloro-4-hydroxy-benzoate (200 mg, 92.5percent yield) as a yellow solid which was used directly without further purification.To a solution of 2-chloro-4-hydroxybenzoic acid (200.0 mg, 1.16 mmol) in methanol (5 mL) was added thionyl chloride (413.6 mg, 3.48 mmol) dropwise at 0 °C. The reaction mixture was stirred at 70°C for 2 h and concentrated. The residue was diluted withwater (15 mL) and extracted with EtOAc (15 mL x 2). The organic layers were combined and washed with water (30 mL x 2) and brine (20 mL). The organic layers were separated, dried over Na2504 and concentrated to obtain methyl 2-chloro-4-hydroxy-benzoate (200 mg, 92.5percent yield) as a yellow solid which was used directly without further purification.2-chloro-4-hydroxybenzoic acid (98.0 g, 46.4 mmol) was treated with concentrated H

Molecular Weight:186.59
XLogP3:3.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:186.0083718
Monoisotopic Mass:186.0083718
Topological Polar Surface Area:46.5
Heavy Atom Count:12
Complexity:172
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes