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0 °C

2-(hydroxymethyl)-5-(methylsulfonyl)phenol (0.2 g, 1.0 mmol) was dissolved in EtOH (4.5 ml) and chloroacetaldehyde (0.15 ml, 1.2 mmol) was added. The mixture was cooled to 0° C. and concentrated H2SO4 (2.5 ml) was added dropwise. The reaction mixture was stirred at 0° C. for 10 min and then in room temperature for 2-3 h. Chloroacetaldehyde (50 μl) and concentrated H2SO4 (0.5 ml) was added and the reaction mixture was stirred for another 1-2 h before the reaction was quenched with water. The aqueous phase was extracted with EtOAc and the combined organic phases were dried (Na2SO4) and evaporated under reduced pressure to give an oil. Purification by flash column chromatography (isooctane/EtOAc 2:1) gave the title compound (0.58 g, with some inpurities). MS m/z (rel. intensity, 70 eV) 264 (M+, 5), 262 (M+, 13), 213 (31), 184 (bp), 77 (61), 51 (47).

1. waitin room temperature for 2-3 h
2. stirringthe reaction mixture was stirred for another 1-2 h before the reaction
3. customwas quenched with water
4. extractionThe aqueous phase was extracted with EtOAc
5. dry with materialthe combined organic phases were dried (Na2SO4)
6. customevaporated under reduced pressure
7. customto give an oil
8. customPurification by flash column chromatography (isooctane/EtOAc 2:1)