5-chloro-2-methoxy-phenol Chemical Properties

Melting point:

161-163.5℃

Boiling point:

237-239℃ (760 Torr)

Density 

1.280±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

form 

crystalline powder

pka

9.01±0.10(Predicted)

color 

Creamy to faint tan

Safety Information

Risk Statements 

41

Safety Statements 

26-39

HS Code 

2907290090

5-chloro-2-methoxy-phenol Usage And Synthesis

Synthesis

General procedure for the synthesis of 5-chloro-2-methoxyphenylboronic acid as a raw material for the synthesis of 5-chloro-2-methoxyphenol: 5-chloro-2-methoxyphenylboronic acid (5.0 g, 26.82 mmol) was dissolved in water (20 mL) at room temperature, followed by the addition of sodium hydroxide pellets (1.6 g, 40.23 mmol). The reaction mixture was stirred for 20 min and then sodium bicarbonate solution (20 mL) was added, followed by acetone (50 mL) and EDTA (0.8 g, 2.68 mmol). The mixture was cooled to 0°C and Oxone? (18.0 g, 29.51 mmol) was added. The mixture was slowly warmed to room temperature over 24 h. Sodium sulfite (1.20 g) was subsequently added, followed by concentrated hydrochloric acid (15 mL) and EtOAc (30 mL). The organic and aqueous phases were separated and the aqueous phase was re-extracted with EtOAc (30 mL). The organic phases were combined, dried with magnesium sulfate, and concentrated under reduced pressure to remove the solvent to afford the target product 5-chloro-2-methoxyphenol in a yield of 4.0 g (95% yield). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 3.90 (3H, s), 5.60 (1H, s), 6.80 (1H, d), 6.90 (1H, d), 6.95 (1H, s).

References

[1] Patent: WO2006/67587, 2006, A2. Location in patent: Page/Page column 22; 23
[2] Patent: US6207662, 2001, B1

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