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0 °C

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 on 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 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).

1. temperatureThe mixture was warmed
2. temperatureto reflux for overnight
3. extractionExtraction by ethyl acetate (100 ml×6)
4. dry with materialThe combined organic phases were dried over MgSO4
5. concentrationThe filtrate was concentrated on vacuo
6. customThe product was triturated by ethyl ether