Potassium Iodide → 4-(3,5-Bis-hydroxymethyl-phenoxy)-butyric acid methyl ester

Participants

Reaction Steps

To a solution of 3,5-bis-hydroxymethylphenol (Felder, D.; Gutiérrez Nava, M.; del Pilar Carreon, M.; Eckert, J. F.; Luccisano, M.; Schell, C.; Masson, P.; Gallani, J. L.; Heinrich, B.; Guillon, D.; Nierengarten, J. F. Helv. Chimica Acta 2002, 85, 288) (200 mg), potassium iodide (50 mg) and potassium carbonate (540 mg) in THF (2.5 mL) was added 4-bromo-butyric acid methyl ester (400 μL). The reaction mixture was stirred for 20 h at room temperature then the unsoluble part was filtered off. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography (Merck SuperVarioFlash 30 g column, Si60 15-40 μm), using gradient elution with a mixture of MeOH (A)/DMC (B), (gradient: 100% B down to 5% A: 95% B) to give 4-(3,5-bis-hydroxymethyl-phenoxy)-butyric acid methyl ester (53.5 mg): LC/MS (Method A2: ES: m/z=255 MH+; m/z=237 (M+H−H2O)+; RT=2.5 min; 1H N.M.R. (400 MHz, DMSO-d6, δ in ppm): δ=1.96 (m, 2H); 2.47 (t, J=6.5 Hz, 2H); 3.61 (s, 3H); 3.96 (t, J=6.5 Hz, 2H); 4.43 (d, J=6.0 Hz, 4H); 5.11 (t, J=6.0 Hz, 2H); 6.71 (s, 2H); 6.82 (s, 1H).

Provenance & Evidence