Uses
6-Methoxy-1-indanone was used in the synthesis of 5-methoxyninhydrin (2,2-dihydroxy-5-methoxy-1,3-indanedione).
Synthesis
General procedure for the synthesis of 6-methoxy-1-indanone from 3-(4-methoxyphenyl)propionic acid: trifluoromethanesulfonic acid (3 eq.) was slowly added to a solution of 3-(4-methoxyphenyl)propionic acid (0.5 mmol) dissolved in anhydrous CH2Cl2 (1.0 mL) in a 12 mL Q-tubepressure tube (provided by QLabtech). The reaction mixture was then warmed to room temperature. A PTFE septum was placed on top of the reaction tube and sealed with the appropriate cap and pressure adapter. The sealed reaction tube was heated in an oil bath at 80°C. The reaction process was monitored by thin layer chromatography (TLC) and gas chromatography-mass spectrometry (GC/MS) until the feedstock completely disappeared. After completion of the reaction, the mixture was poured into ice water and extracted three times with CH2Cl2. The organic phases were combined, dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure. Finally, the target compound 6-methoxy-1-indanone was purified from the crude product by fast column chromatography.
References
[1] Molecules, 2014, vol. 19, # 5, p. 5599 - 5610
[2] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 5, p. 470 - 475
[3] Organic and Biomolecular Chemistry, 2017, vol. 15, # 35, p. 7374 - 7379
[4] Synthetic Communications, 1991, vol. 21, # 21, p. 2231 - 2256
[5] Tetrahedron Letters, 2004, vol. 45, # 8, p. 1741 - 1745
