2,3-DIHYDRO-1-BENZOFURAN-2-YLMETHANOL Chemical Properties

Boiling point:

120-122

Density 

1.181 g/cm3(Temp: 16 °C)

storage temp. 

Sealed in dry,Room Temperature

form 

Oil

pka

14.22±0.10(Predicted)

color 

Colorless

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

Hazard Note 

Harmful

HazardClass 

IRRITANT

HS Code 

2932990090

2,3-DIHYDRO-1-BENZOFURAN-2-YLMETHANOL Usage And Synthesis

Chemical Properties

2,3-dihydrobenzofuran-2-methanol is Colorless Oil

Uses

2-Hydroxymethyl-2,3-dihydrobenzofuran (H947870) is a reactant used in the preparation of thromboxane A2 agonist indane derivatives.

Uses

2,3-dihydrobenzofuran-2-methanol is a reactant used in the preparation of thromboxane A2 agonist indane derivatives.

Synthesis

2-Allylphenol (5) (200 mg, 1.49 mmol) was used as a raw material, which was mixed with m-chloroperoxybenzoic acid (616 mg, 3.57 mmol) in dichloromethane (DCM, 30 mL) and the reaction was stirred for 6 hours at room temperature. Subsequently, potassium carbonate (K2CO3, 617 mg, 4.47 mmol) and methanol (25 mL) were added to the reaction system and stirring was continued for 14 hours. After completion of the reaction, the solvent was removed by evaporation and diluted by adding water (15 mL). The mixture was extracted with dichloromethane (3 x 20 mL), the organic phases were combined, washed with brine (10 mL), dried over anhydrous sodium sulfate (Na2SO4), and the solvent was evaporated again. The crude product was purified by fast column chromatography (eluent: ethyl acetate/hexane=1:7) to afford the target compound (2,3-dihydrobenzofuran-2-yl)methanol (6) (195 mg, 87% yield) as a light yellow oil. The structure of the product was confirmed by 1H NMR (CDCl3, 300 MHz) and FTIR (neat): 1H NMR δ 7.17 (d, 1H, J = 7.4 Hz), 7.11 (t, 1H, J = 7.6 Hz), 6.85 (t, 1H, J = 7.4 Hz), 6.79 (d, 1H, J = 7.4 Hz), 4.91 (m, 1H) , 3.85 (dd, 1H, J = 12.0, 3.2 Hz), 3.74 (dd, 1H, J = 12.0, 6.3 Hz), 3.25 (dd, 1H, J = 15.5, 9.4 Hz), 3.01 (dd, 1H, J = 15.5, 7.4 Hz); FTIR 3391, 3049, 1047 cm-1.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 12, p. 2545 - 2549
[2] Advanced Synthesis and Catalysis, 2007, vol. 349, # 17-18, p. 2685 - 2689
[3] Bioorganic and medicinal chemistry letters, 1999, vol. 9, # 3, p. 401 - 406
[4] Tetrahedron Asymmetry, 2000, vol. 11, # 16, p. 3375 - 3393
[5] Synthesis (Germany), 2017, vol. 49, # 18, p. 4254 - 4260

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