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Table 1 Optimization of the reaction conditions following Figure 1

From: Facile synthesis of symmetrical bis(benzhydryl)ethers using p-toluenesulfonyl chloride under solvent-free conditions

Entry p-TsCl (mol%) Solvent Temperature (°C) Time (min) Yield (%) a
1 0 - 110 120 No reaction
2 10 - 90 25 82
3 10 - 110 15 87
4 5 - 90 35 80
5 5 - 110 15 86
6 5 - Rt 240 Trace
7 3 - 110 75 28
8 10 CH2Cl2 Rt 1,050 19
9 5 CH2Cl2 Rt 1,050 Trace
10 10 THF Rt 600 Trace
11 10 CH3CN Rt 720 17
12 10 CH2Cl2 Reflux 300 36
13 50 - 110 5 43 (tosylate: 47)
14 100 - 110 5 7 (tosylate: 91)
  1. aIsolated yield; RT, room temperature; p-TsCl, p-toluenesulfonyl chloride; Tosylate, benzhydryl p-toluenesulfonate.