3-(HYDROXYMETHYL)BENZALDEHYDE Chemical Properties

Melting point:

120℃

Boiling point:

282℃

Density 

1.184

Flash point:

118℃

storage temp. 

2-8°C, stored under nitrogen

pka

14.10±0.10(Predicted)

form 

solid

Appearance

Colorless to off-white Liquid

3-(HYDROXYMETHYL)BENZALDEHYDE Usage And Synthesis

Synthesis Reference(s)

Journal of the American Chemical Society, 105, p. 7175, 1983 DOI: 10.1021/ja00362a028

Synthesis

General procedure for the synthesis of 3-(hydroxymethyl)benzaldehyde from m-toluenedicarboxaldehyde: NaBH4 (1.7 g) was slowly added to a mixed solution of ethanol (100 mL) and tetrahydrofuran (150 mL) of m-toluenedicarboxaldehyde (1b, 20.0 g). The reaction mixture was stirred under ice bath conditions for 6 hours. Upon completion of the reaction, the pH was adjusted to 5-6 with 2 M hydrochloric acid solution to quench the reaction. Subsequently, the solvent was removed by rotary evaporator and the residue was extracted by adding water and ethyl acetate to the residue. The organic phase was washed with saturated NaCl solution and dried with anhydrous Na2SO4 for 8 hours. Finally, the product was purified by silica gel column chromatography using petroleum ether-ethyl acetate (5:1, v/v) as eluent to afford the target compound 3-(hydroxymethyl)benzaldehyde (2b, 16.4 g, 80.2% yield).

References

[1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 45, p. 10688 - 10694
[2] Journal of Organometallic Chemistry, 2010, vol. 695, # 1, p. 82 - 89
[3] Dalton Transactions, 2015, vol. 44, # 9, p. 4054 - 4062
[4] Molecules, 2016, vol. 21, # 7,
[5] Patent: CN107522647, 2017, A. Location in patent: Paragraph 0082; 0083

3-(HYDROXYMETHYL)BENZALDEHYDE(52010-98-7)Related Product Information

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