3-HYDROXY-4-METHYL-BENZALDEHYDE Chemical Properties

Melting point:

73-74 °C

Boiling point:

252.4±20.0 °C(Predicted)

Density 

1.175±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

9.59±0.10(Predicted)

Appearance

Off-white to yellow Solid

InChI

InChI=1S/C8H8O2/c1-6-2-3-7(5-9)4-8(6)10/h2-5,10H,1H3

InChIKey

DHVJHJQBQKKPNB-UHFFFAOYSA-N

SMILES

C(=O)C1=CC=C(C)C(O)=C1

Safety Information

Hazard Codes 

Xi

Risk Statements 

41

Safety Statements 

26-39

HS Code 

2912490090

3-HYDROXY-4-METHYL-BENZALDEHYDE Usage And Synthesis

Synthesis

General procedure for the synthesis of compounds (CAS:57295-30-4) from 5-(hydroxymethyl)-2-methylphenol: The product of step (i) (440.0 mg, 3.18 mmol) was dissolved in THF (4.4 mL) at room temperature, followed by addition of MnO2 (552.9 mg, 6.36 mmol). The reaction mixture was stirred at 50 °C for 6 hours. Upon completion of the reaction, the mixture was filtered through a diatomaceous earth pad to remove solid impurities. The filtrate was concentrated and the residue was purified by fast column chromatography to afford the target compound (CAS:57295-30-4) (46.1 mg, 11% yield) as a light yellow solid.1H NMR (CDCl3) δ: 9.90 (1H, s), 7.36 (1H, dd, J = 7.76, 1.44 Hz), 7.30 (1H, s ), 7.29 (1H, d, J = 5.52 Hz), 5.33 (1H, s), 2.33 (3H, s).

Purification Methods

Crystallise it from water or *C6H6 (m 71-71o). The O-methyl ether has m 45-46o (from Et2O/hexane). [Sedgwick & Allott J Chem Soc 2820 1923, Flitsch et al. Justus Liebigs Ann Chem 1413 1985, Beilstein 8 H 100, 8 II 103, 8 IV 368.]

References

[1] Patent: US2011/136801, 2011, A1. Location in patent: Page/Page column 44

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