| 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 |
