Synthetic Route of 495-76-1, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.495-76-1, name is Benzo[d][1,3]dioxol-5-ylmethanol, molecular formula is C8H8O3, molecular weight is 152.1473, as common compound, the synthetic route is as follows.
To a solution of the piperonyl alcohol (8) (2.0 g, 13.15 mmol) in anhydrous CH2Cl2 (30 mL), cooled to 0 C and stirred, under an argon atmosphere, freshly distilled PBr3 (3.7 mL, 39.45 mmol), was added dropwise. The resulting solution was kept under stirring at 0 C for a further 20 minutes. After, the ice bath was removed, maintaining the stirring for a further 2 h. The system was cooled again to 0 C and a saturated solution of NaHCO3 (75 mL) was slowly added. Extraction was carried out with ethyl ether (3x 70 mL). The combined organic phases were washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford crude bromide (9). This bromide (used immediately after its preparation) was solubilized with anhydrous acetonitrile (30 mL), treated with triphenylphosphine (3.45 g, 13.15 mmol) and stirred overnight, under reflux. Acetonitrile was removed under reduced pressure and the residue was recrystallized from ethanol to provide (5.21 g) Wittig salt (10) in 83% overall yield. Rf 0.53 (CH2Cl2/MeOH 9:1). mp: 237.2-238.5 C. IR (neat) numax/cm-1: 3018, 1492, 1438, 1246, 1109, 750, 687. 1H NMR (400 MHz, CDCl3) delta 7.80-7.62 (m, 15H), 6.62-6.59 (m, 1H), 6.53 (d, 2H, J=5.5 Hz), 5.87 (s, 2H), 5.28 (d, 2H, J=13.9 Hz). 13C NMR (100 MHz, CDCl3) delta 147.6, 134.9 (d, J=11.5 Hz), 134.2 (d, J=38.6 Hz), 130.0 (d, J=49.7 Hz), 125.3, 119.9 (d, J=36 Hz), 118.0, 117.2, 111.2 (d, J=18.4 Hz), 108.4 (d, J=13.5 Hz), 101.1, 30.4 (d, J=187.4 Hz). HRMS (ESI+) calcd for C26H22BrO2P [M-HBr]+ 397.1352, found 397.1358.
Statistics shows that 495-76-1 is playing an increasingly important role. we look forward to future research findings about Benzo[d][1,3]dioxol-5-ylmethanol.
Reference:
Article; Diaz-Munoz, Gaspar; Isidorio, Raquel Geralda; Miranda, Izabel Luzia; de Souza Dias, Gabriel Nunes; Diaz, Marisa Alves Nogueira; Tetrahedron Letters; vol. 58; 33; (2017); p. 3311 – 3315;,
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