Synthesis
The general procedure for the synthesis of 3-methyl-2,4-dihydroxybenzaldehyde from 2,6-dihydroxytoluene and N,N-dimethylformamide was as follows: first, N,N-dimethylformamide (6.2 mL, 80.65 mmol) was mixed with phosphorochloride (8.1 mL, 88.61 mmol), followed by the addition of 2-methylresorcinol (5.0 g, 40.3 mmol ) and ethyl acetate (100 mL). The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the reaction solution was combined with ethyl acetate, the organic phase was dried with anhydrous sodium sulfate, filtered to remove the desiccant, and the filtrate was subsequently concentrated under reduced pressure. Finally, the target product 3-methyl-2,4-dihydroxybenzaldehyde (4.9 g, 79.9% yield) was purified by silica gel column chromatography.
References
[1] Organic and Biomolecular Chemistry, 2005, vol. 3, # 12, p. 2305 - 2309
[2] Chemistry - An Asian Journal, 2010, vol. 5, # 1, p. 130 - 140
[3] Patent: CN106957279, 2017, A. Location in patent: Paragraph 0042; 0049; 0050; 0051
[4] Tetrahedron Letters, 2000, vol. 41, # 11, p. 1741 - 1745
[5] Angewandte Chemie - International Edition, 2017, vol. 56, # 42, p. 12888 - 12891
