반응 #8518

반응 방정식

p-xylylenebis(tetrahydrothiophenium chloride)

sodium t-butoxide

octanethiol

hydrochloric acid

p-bis(octylthiomethyl)benzene

→

p-(Octylthiomethyl)benzyl chloride

용매

methanol

methanol

반응 조건

후처리

1. 1
   workup.WAITAfter one hour
2. 2
   기타all the volatile components were removed under reduced pressure
3. 3
   여과the undissolved constituents were filtered off
4. 4
   기타the filtrate was evaporated under reduced pressure
5. 5
   workup.ADDITIONThe oil was mixed with twice the volume of octane
6. 6
   workup.DISTILLATIONdistilled off under reduced pressure together with tetrahydrothiophene
7. 7
   기타finally giving 5.31 g

실험 절차

1.83 g (19 mmol) of sodium t-butoxide and 2.78 g (19 mmol) of octanethiol were stirred into 40 g of methanol at room temperature. After 30 minutes, the clear solution was added in one portion to 6.68 g (19 mmol) of the p-xylylenebis(tetrahydrothiophenium chloride) obtained in accordance with Example 1, in 100 g of methanol. After one hour, the mixture was neutralized using 1N hydrochloric acid, and all the volatile components were removed under reduced pressure. The crude product was taken up in 200 ml of chloroform, the undissolved constituents were filtered off, and the filtrate was evaporated under reduced pressure. The oil was mixed with twice the volume of octane, and distilled off under reduced pressure together with tetrahydrothiophene. This sequence was repeated three times with octane, finally giving 5.31 g, consisting of 90% of product, 5% of starting material and 5% of p-bis(octylthiomethyl)benzene. This reaction was carried out at various temperatures and the product distribution analyzed by 1H-NMR spectroscopy (all data in mol-%).

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