2-hydroxy-4-Methoxytoluene Chemical Properties

Melting point:

44 °C

Boiling point:

249-250 °C

Density 

1.078±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

9.93±0.10(Predicted)

Appearance

Off-white to yellow <44°C Solid,>44°C Liquid

InChI

InChI=1S/C8H10O2/c1-6-3-4-7(10-2)5-8(6)9/h3-5,9H,1-2H3

InChIKey

QXIOWYFFTWXSHE-UHFFFAOYSA-N

SMILES

C1(O)=CC(OC)=CC=C1C

Safety Information

HS Code 

2909500090

2-hydroxy-4-Methoxytoluene Usage And Synthesis

Synthesis Reference(s)

Tetrahedron Letters, 29, p. 3741, 1988 DOI: 10.1016/S0040-4039(00)82103-6

Synthesis

Example 84 Steps for the synthesis of ethyl 3-[4-(5-hydroxy-2-methylphenoxy)-2-methylphenyl]-propionate: Step A Preparation of 5-methoxy-2-methylphenol A solution of 2-hydroxy-4-methoxybenzaldehyde (5.00 g, 32.86 mmol), carbon-loaded palladium (10%, 3.50 g, 3.28 mmol) in ethanol (32 mL), and acetic acid (3 mL) was placed in a reactor and the reaction mixture was stirred at 60 psi hydrogen pressure. After overnight reaction, the mixture was filtered through a diatomaceous earth pad and washed with methanol. The filtrate was concentrated under reduced pressure and the resulting crude product was purified by fast column chromatography with hexane:ethyl acetate (2:1) as eluent to give 5-methoxy-2-methylphenol (3.96 g, 87% yield). Thin layer chromatography (TLC) Rf = 0.58 (unfolding agent: hexane:ethyl acetate 2:1).1H NMR (300MHz, CDCl3) δ: 2.18 (s, 3H), 3.75 (s, 3H), 6.42 (m, 2H), 7.00 (d, 1H, J = 8.9Hz).

References

[1] Patent: WO2005/37763, 2005, A1. Location in patent: Page/Page column 130-131
[2] Tetrahedron Letters, 1988, vol. 29, # 31, p. 3741 - 3744
[3] Monatshefte fuer Chemie, 1964, vol. 95, p. 649 - 670
[4] Journal of Organic Chemistry, 1980, vol. 45, # 2, p. 208 - 212
[5] Patent: US2003/207916, 2003, A1

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