4-(4-Chlorophenoxy)phenol Chemical Properties

Melting point:

80-85 °C

Boiling point:

169°C/2.5mmHg(lit.)

storage temp. 

2-8°C

form 

powder to crystal

color 

White to Light yellow to Light orange

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-41-43

Safety Statements 

26-36/37/39

WGK Germany 

3

HS Code 

2909.50.5000

4-(4-Chlorophenoxy)phenol Usage And Synthesis

Chemical Properties

Light yellow solid

Synthesis

Step 2; 4-(4-Chlorophenoxy)phenol; Following the general procedure of Example 12 (Step 2), boron tribromide (1.0 M dichloromethane solution, 9.66 mL, 9.66 mmol) was added to a solution of dichloromethane (15 mL) of the product of Step 1 (0.76 g, 3.22 mmol), and the reaction was completed to give 4-(4-chlorophenoxy)phenol ( 0.37 g, 52%), the product was a light green solid. Step 2; 4-(4-Chlorophenoxy)phenol; To a solution of dichloromethane (50 mL) of the product of Step 1 (2.86 g, 12.18 mmol) was added boron tribromide (1.0 M solution in dichloromethane, 30 mL, 30.5 mmol) dropwise over 5 min at -78 °C. The reaction mixture was stirred at -78°C for 1 hour, then warmed to ambient temperature and continued stirring for 1 hour. Upon completion of the reaction, the mixture was cooled to 0 °C and slowly added to cold water/dichloromethane (50 mL/50 mL). The organic phase was washed sequentially with water and brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by rapid chromatography on silica gel using hexane/EtOAc (gradient elution) to afford 4-(4-chlorophenoxy)phenol (2 g, 75%); 1H NMR (400 MHz, CDCl3) δ 4.8 (s, 1H), 7.23-7.26 (m, 2H), 6.81-6.92 (m, 6H). Step 2; 4-(4-Chlorophenoxy)phenol; Boron tribromide (7.6 mL, 80.3 mmol) was added dropwise over 5 min at -78 °C to a solution of dichloromethane (72 mL) of the product of step 1 (6.3 g, 26.8 mmol). The reaction mixture was stirred at -78 °C for 1 hour, then warmed to ambient temperature and continued stirring for 1 hour. Upon completion of the reaction, the mixture was cooled to 0 °C and slowly added to cold water/dichloromethane. The organic phase was washed sequentially with water and brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by rapid chromatography on silica gel using EtOAc/hexane (gradient elution) to afford 4-(4-chlorophenoxy)phenol (4.50 g, 76%).

References

[1] Patent: US2007/66820, 2007, A1. Location in patent: Page/Page column 25; 27; 29
[2] Barell-Festschr. S. 266, 269, 272, 273,
[3] Organic Process Research and Development, 2009, vol. 13, # 6, p. 1177 - 1184
[4] Patent: WO2011/11598, 2011, A1. Location in patent: Page/Page column 16
[5] Chem.Abstr., 1976, vol. 85, # 20843,

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