Entry Temp. (°C) TBAOH (mL) Thioether Ether
  Time (min) Yield (%)* Time (min) Yield (%)b
1 50 0.5 400 70 380 72
2 50 1.0 240 77 260 75
3 50 1.5 110 85 100 81
4 50 2.0 70 90 80 92
5 50 2.5 70 90 80 91
6 25 2.0 400 30 400 25
7 40 2.0 400 74 400 65
aModel reaction conditions: molar ratio of benzyl alcohol (benzyl mercaptan)/acetic anhydride(acetic anhydride) was 1.5 (1.0)/1.0 (1.5). The reactions run in the presence of TBAOH (20% in water) without any extra solvent under an air atmosphere conditions
bYield refer to an isolated yield by preparative chromatography
Table 1: Optimization of TBAOH amount and temperature of reactiona.