反応 #6629

反応方程式

phenyl-3-methylbut-2-enylsulfide

Compound 60

phenyl-3-methylbut-2-enylsulfide

phosphorus pentoxide

phosphoric acid

benzene

→

title compound

4,4-Dimethylthiochroman

反応条件

後処理

1. 1
   温度This solution was refluxed
2. 2
   その他The supernatant organic layer was decanted
3. 3
   抽出the syrupy residue extracted with 3×50ml ether
4. 4
   洗浄washed with water, saturated NaHCO3 and saturated NaCl solutions
5. 5
   乾燥dried (MgSO4)
6. 6
   その他Solvent was removed in vacuo
7. 7
   workup.DISTILLATIONthe residue purified by kugelrohr distillation (80 degrees C., 0.5mm)

実験手順

To a solution of 15.48g (86.824 mmol) of phenyl-3-methylbut-2-enylsulfide (Compound 60) in 160ml benzene were added successively 12.6g (88.767mmol) of phosphorus pentoxide and 11 ml of 85% phosphoric acid. This solution was refluxed with vigorous stirring under argon for 20 hours, then cooled to room temperature. The supernatant organic layer was decanted and the syrupy residue extracted with 3×50ml ether. Organic fractions were combined and washed with water, saturated NaHCO3 and saturated NaCl solutions and then dried (MgSO4). Solvent was removed in vacuo and the residue purified by kugelrohr distillation (80 degrees C., 0.5mm) to give the title compound as a pale yellow oil. PMR (CDCl3) :& 1.30 (6H, s), 1.90-1.95 (2H, m), 2.95-3.00 (2H, m), 6.96-7.00 (2H, m), 7.04-7.07 (1H, m), 7.30-7.33 (1H, m).

出典