(4-propan-2-yloxyphenyl)methanol Chemical Properties

Melting point:

27-28 °C

Boiling point:

144-146 °C(Press: 12 Torr)

Density 

1.034±0.06 g/cm3(Predicted)

storage temp. 

Store at room temperature

pka

14.68±0.10(Predicted)

Appearance

Colorless to light yellow Liquid

Safety Information

HS Code 

2909498090

(4-propan-2-yloxyphenyl)methanol Usage And Synthesis

Synthesis Reference(s)

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

Synthesis

To a methanolic solution of 4-isopropoxybenzaldehyde (0.93 g, 5.6 mmol) in methanol (20 mL) was slowly added a methanolic solution of sodium tetrahydroborate (0.32 g, 11 mmol) under cooling conditions in an ice bath. The reaction mixture was stirred at room temperature for 4 hours. Upon completion of the reaction, the reaction solution was acidified by adding 2N hydrochloric acid to the reaction solution and subsequently extracted with ether. The organic phases were combined, washed with water and concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 7:3) to afford the target product (4-isopropoxyphenyl) methanol (0.76 g, 81% yield) as a colorless oil.1H NMR (CDCl3) δ: 1.33 (6H, d, J = 6.1 Hz), 4.55 (1H, quintet, J = 6.1 Hz), 4.61 (2H, s), 6.85-6.91 (2H, m), 7.25-7.30 (2H, m).

References

[1] Tetrahedron Letters, 2015, vol. 56, # 46, p. 6460 - 6462
[2] ChemMedChem, 2016, vol. 11, # 13, p. 1415 - 1427
[3] Patent: EP1688138, 2006, A1. Location in patent: Page/Page column 106
[4] Tetrahedron, 2013, vol. 69, # 2, p. 933 - 941

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