Dimethylformamide → Benzaldehyde, p-phenylthio-

Participants

Reaction Steps

Into a dimethylformamide (DMF) solution (30 mL) of 11.0 g (100 mmol) of benzenethiol is gradually added 14.0 g (132 mmol) of anhydrous Na2CO3 at 85° C. Then 4-chlorobenzaldehyde (11.3 g, 80.0 mol) is added during 20 min. at 85° C. The reaction solution is stirred at this temperature for 3 h. After adding H2O into the reaction mixture, the crude product is extracted with ethyl acetate. The organic layer is washed twice with H2O and with brine, dried over anhydrous MgSO4 and condensed. The residue is applied to column chromatography on silica gel with acetone-hexane (from 1:30 to 1:10) as eluent. 6.05 g of pale yellow oil are obtained (35%). The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 7.24 (d, 2H), 7.42-7.44 (m, 3H), 7.53 (dd, 2H), 7.71 (d, 2H), 9.96 (s, 1 H).

Provenance & Evidence