4-CHLORO-3-HYDROXY-BENZOIC ACID METHYL ESTER

4-CHLORO-3-HYDROXY-BENZOIC ACID METHYL ESTER Property

Melting point:

100-101 °C

Boiling point:

288.3±20.0 °C(Predicted)

Density 

1.354±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

7.68±0.10(Predicted)

Appearance

Light brown to brown Solid

Safety

HS Code 

2918290090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

4-CHLORO-3-HYDROXY-BENZOIC ACID METHYL ESTER Chemical Properties,Usage,Production

Uses

4-Chloro-3-hydroxybenzoic Acid Methyl Ester id used in the synthesis of antidepressants.

Synthesis

The general procedure for the synthesis of methyl 3-hydroxy-4-chlorobenzoate from methanol and 4-chloro-3-hydroxybenzoic acid was as follows: thionyl chloride (6 g) was added slowly and dropwise to a methanol (100 mL) solution of 4-chloro-3-hydroxybenzoic acid (4.4 g, 25.50 mmol). The reaction mixture was stirred at 70 °C for 2 hours. Upon completion of the reaction, the reaction solution was concentrated under reduced pressure to remove the solvent. The concentrated residue was diluted by adding hexane (50 mL) to the concentrated residue. The precipitated solid product was collected by filtration and dried in an oven under reduced pressure to afford methyl 3-hydroxy-4-chlorobenzoate as a light yellow solid (4 g, 84% yield). The product was analyzed by LC/MS (electrospray ionization, m/z): [M+H]+ 187.0. 1H NMR (300 MHz, DMSO-d6) δ 10.69 (s, 1H, OH), 7.55 (d, J=2.10 Hz, 1H, ArH), 7.49 (d, J=8.40 Hz, 1H, ArH), 7.36-7.40 ( m, 1H, ArH), 3.83-3.85 (d, J=8.40Hz, 3H, OCH3).

References

[1] Chemical and Pharmaceutical Bulletin, 1994, vol. 42, # 11, p. 2365 - 2369
[2] Patent: WO2014/66795, 2014, A1. Location in patent: Paragraph 0175
[3] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 13, p. 3141 - 3147
[4] Journal of Medicinal Chemistry, 2005, vol. 48, # 9, p. 3290 - 3312
[5] Patent: EP2048140, 2009, A1. Location in patent: Page/Page column 25