Uses
2,3-Dimethylanisole is used as starting reagent in the synthesis of biphenyl-indanone A, a positive allosteric modulator of the metabotropic glutamate receptor subtype 2. It can be used to produce 2-methoxy-6-methyl-benzaldehyde by heating.
Synthesis
General procedure: 1-methoxy-2,3-dimethylbenzene was synthesized by alkylation of 2,3-dimethylphenol with dimethyl carbonate. The specific operation was as follows: 3 mmol of Mn2(CO)10, W(CO)6 or Co2(CO)8 catalyst, 100 mmol of 2,3-dimethylphenol, and 300 mmol of dimethyl carbonate were sequentially added to a 17 mL stainless steel high-pressure microreactor. After sealing the reactor, the reaction was heated at 180 °C for 1 hour. Upon completion of the reaction, the reactor was cooled to room temperature, opened and the reaction mixture was filtered through an alumina layer. The unreacted dimethyl carbonate was removed by distillation, and the residue was distilled under atmospheric or reduced pressure conditions or recrystallized using ethanol to obtain the target product 1-methoxy-2,3-dimethylbenzene. The yield of the reaction was 99% and the boiling point of the product was 95.8-96 °C (30 mmHg).13C NMR data (δC, ppm): 11.99 (CH3), 20.56 (CH3), 55.83 (OCH3), 110.02 (C6), 122.43 (C4), 124.78 (C2), 128.74 (C5). 137.70 (C3), 157.36 (C1). Elemental analysis results (measured values): C 79.29%, H 8.82%; calculated values for molecular formula C9H12O: C 79.37%, H 8.88%.
References
[1] Russian Journal of Organic Chemistry, 2015, vol. 51, # 3, p. 330 - 334
[2] Methylation of Phenol and Its Derivatives with Dimethyl Carbonate in the Presence of Mn2(CO)10, W(CO)6, and Co2(CO)8, 2015, vol. 51, # 3, p. 330 - 334,5
