Synthesis of rubrene from 1,1,3 triphenylprop-2-yn-1-ol
1,1,3-triphenylprop-2-yn-1-ol 2g 4g 6g 8g 10g
Dichloromethane (39.4 °C) 15ml 30ml 45ml 60ml 75ml
Triethylamine 1.1ml 2.2ml 3.3ml 4.4ml 5.5ml
Methanesulphonyl chloride (161 °C) 1.2ml 2.4ml 3.6ml 4.8ml 6.0ml
Collidine (171 – 172 °C) 1ml 2ml 3ml 4ml 5ml
Xylene (140 °C)
2.0 g 1,1,3-triphenylprop-2-yn-1-ol is dissolved in 15 ml anhydrous dichloromethane under nitrogen and cooled to 0 °C
1.1 ml anhydrous triethylamine and 1.2ml methanesulphonyl chloride were added and the mixture stirred for 1 hour at 0 °C, then allowed to warm to
room temperature
The mixture was heated at reflux to distil off the dichloromethane which was gradually replaced with xylene
The solution was heated and on reaching 80 °C 1ml collidine added dropwise
Reaction temperature raised to 95 °C and held at this temperature for 7 hours
Mixture allowed to cool to room temperature and the precipitate collected by filtration
The red soldid was recrystallized from ethanol to afford the desired product yield 0.76 g (46%)
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