(4-Chloro-3-Methoxyphenyl)Methanol

(4-Chloro-3-Methoxyphenyl)Methanol Property

Boiling point:

279.2±25.0 °C(Predicted)

Density 

1.239±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

14.04±0.10(Predicted)

Appearance

White to off-white Solid

Safety

HS Code 

2909498090

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-Methoxyphenyl)Methanol Chemical Properties,Usage,Production

Synthesis Reference(s)

Journal of Medicinal Chemistry, 32, p. 1757, 1989 DOI: 10.1021/jm00128a016

Synthesis

Step 1. Dissolve 4-chloro-3-methoxybenzoic acid (1.12 g, 5.98 mmol) in tetrahydrofuran (30 mL) under ice bath conditions with stirring. A tetrahydrofuran solution of 1.0 M lithium aluminum hydride (7.18 mL, 7.18 mmol) was slowly added over approximately 5 minutes. Ice bath conditions were maintained and stirring of the reaction mixture was continued for 2 hours. Upon completion of the reaction, the reaction was quenched by slow dropwise addition of water (0.27 mL), followed by addition of 15% aqueous sodium hydroxide solution (0.27 mL), and finally water (0.82 mL). The resulting suspension was filtered and the collected solid was washed with ethyl acetate. The filtrates were combined and concentrated under reduced pressure to give (4-chloro-3-methoxyphenyl)methanol as a colorless oil (737 mg, 71% yield). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 3.92 (s, 3H), 4.67 (s, 2H), 6.87 (d, J = 7.6 Hz, 1H), 6.98 (s, 1H), 7.33 (d, J = 7.6 Hz, 1H).

References

[1] Patent: US2002/77486, 2002, A1
[2] Patent: US6906063, 2005, B2
[3] Patent: EP2314593, 2016, B1. Location in patent: Paragraph 0201
[4] Journal of Medicinal Chemistry, 1987, vol. 30, # 10, p. 1887 - 1891
[5] Journal of Medicinal Chemistry, 1992, vol. 35, # 23, p. 4408 - 4414