Reaktion #80652

Reaktionsgleichung

4-bromo-2-(1,1,3-trimethyl-3-hydroxybutyl) thiophenol

Compound 32

4-bromo-2-(1,1,3-trimethyl-3-hydroxybutyl) thiophenol

H2SO4

→

title compound

2,2,4,4-Tetramethyl-6-bromothiochroman

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturat reflux for 24 h
3. 3
   ExtraktionThe mixture was extracted with hexanes
4. 4
   Waschenwashed successively with water, saturated NaHCO3, water again
5. 5
   Trocknensaturated NaCl and then dried (MgSO4)
6. 6
   SonstigeThe solvent was removed in vacuo
7. 7
   Sonstigethe residue purified by flash chromatography (silica; hexanes)

Vorschrift

A mixture of 500 mg (1.49 mmol) of 4-bromo-2-(1,1,3-trimethyl-3-hydroxybutyl) thiophenol (Compound 32) and 8 ml of 20 percent aqueous H2SO4 was heated at reflux for 24 h. The mixture was extracted with hexanes, the organic extracts were combined and washed successively with water, saturated NaHCO3, water again, saturated NaCl and then dried (MgSO4). The solvent was removed in vacuo and the residue purified by flash chromatography (silica; hexanes) to give the title compound as a colorless oil. PMR (CDCl3): & 1.35 (6H, s), 1.40 (6H, s), 1.93 (2H, s), 7.17 (1H, dd, J-8.4 Hz, 2.1 Hz), 7.23 (1H, d, J-8.4 Hz), 7.26 (1H, d, J-2.1 Hz). MS exact mass, m/e 16 284.0221 (calcd. for C13H17S Br, 284.0234).

Quelle