sodium alpha-hydroxy-p-methoxytoluene-alpha-sulphonate synthesis

Yield:33402-67-4 100%

Reaction Conditions:

with disodium metabisulfite in ethanol at 4 - 20;Inert atmosphere;

Steps:

4.1.2.1. Method A. General procedure for the synthesis of intermediatesodium hydroxy-(4-methoxyphenyl)methanesulfonate, SMS-1.

4-methoxybenzaldehyde (7.34 mmol) and ethanol (22 mL) wereadded to a round-bottom flask equipped with a magnetic stir barunder argon atmosphere; then a 16% solution of Na2S2O5 (5 mL)was added. The reaction mixture was vigorously stirred for 1 h atroom temperature, and kept overnight a 4 C in a refrigerator. Theresulting precipitate was filtered off under vacuum to obtain awhite solid in quantitative yield. 4.1.2.1.1. Sodium hydroxy-(4-methoxyphenyl)methanesulfonate,SMS-1. White crystalline solid (100% yield); thermal decompositionof the compound prohibits melting point measurement. IR(KBr), nmax: 3435, 3200, 2980, 1610, 1517, 1250, 1114, 839 cm1. 1HNMR (C2D6SO): d 3.70 (s, 3H), 4.85 (d, J 5.0 Hz, D2O, 1H), 5.65 (d,J 5.0 Hz, 1H), 6.77 (d, J 8.6 Hz, 2H), 7.31 (d, J 8.6 Hz, 2H). 13CNMR (C2D6SO): d55.8, 83.7, 114.5 (2C), 128.1 (2C), 133.2, 159.2.HRMS (ESI) calcd. for C8H9Na2O5S[MNa]: 262.9961; found:262.9959.

References:

Escala, Nerea;Valderas-García, Elora;Bardón, María álvarez;Gómez de Agüero, Verónica Castilla;Escarcena, Ricardo;López-Pérez, José Luis;Rojo-Vázquez, Francisco A.;San Feliciano, Arturo;Bala?a-Fouce, Rafael;Martínez-Valladares, María;Olmo, Esther del [European Journal of Medicinal Chemistry,2020,vol. 208,art. no. 112554]