Hydrochloric Acid → (2-Benzyloxy-phenyl) methanesulfonic acid

Participants

Reaction Conditions

Reaction Steps

Sodium sulfite (4.2 g) was added to a stirred mixture of 1-benzyloxy-2-bromomethyl-benzene (8.9 g), tetrabutylammonium iodide (59 mg) and water (150 ml). The mixture was warmed to reflux for overnight. As the mixture cooled to 0° C., it was acidified by 6N HCl. Extraction by ethyl acetate (100 ml×6) was performed (some remained in the aqueous layer). The combined organic phases were dried over MgSO4. The filtrate was concentrated in vacuo. The product was triturated by ethyl ether to give (2-benzyloxy-phenyl)-methanesulfonic acid (678 mg, 8%). 1H NMR (400 MHz, DMSO-D6): δ ppm 3.82 (s, 2 H) 5.09 (s, 2 H) 6.86 (t, J=7.45 Hz, 1 H) 6.96 (d, J=8.08 Hz, 1 H) 7.14 (t, J=7.83 Hz, 1 H) 7.32 (d, J=7.33 Hz, 1 H) 7.38 (t, J=7.33 Hz, 2 H) 7.46 (d, J=9.09 Hz, 1 H) 7.52 (d, J=7.07 Hz, 2 H).

Provenance & Evidence