Reaktion #587154

Reaktionsgleichung

water

H2SO4

Water

Hexamethylenetetramine

TFA

4-Bromophenol

→

product

Ausbeute 60.0%

2,6-Diformyl-4-bromophenol

Ausbeute 60.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred under argon for 48 h
2. 2
   TemperaturThe reaction mixture was then cooled to ambient temperature
3. 3
   workup.STIRRINGthe solution stirred for an additional 2 h
4. 4
   Sonstigethe resulting precipitate collected on a Büchner funnel
5. 5
   workup.DISSOLUTIONThe precipitate was dissolved in ethyl acetate (EtOAc)
6. 6
   Trocknenthe solution was dried over MgSO4
7. 7
   FiltrationThe solution was filtered
8. 8
   Sonstigethe solvent removed on a rotary evaporator
9. 9
   SonstigePurification by column chromatography on silica gel (400 g)

Vorschrift

Hexamethylenetetramine (73.84 g, 526 mmol) was added to TFA (240 mL) with stirring. 4-Bromophenol (22.74 g, 131 mmol) was added in one portion and the solution heated in an oil bath to 120° C. and stirred under argon for 48 h. The reaction mixture was then cooled to ambient temperature. Water (160 mL) and 50% aqueous H2SO4 (80 mL) were added and the solution stirred for an additional 2 h. The reaction mixture was poured into water (1600 mL) and the resulting precipitate collected on a Büchner funnel. The precipitate was dissolved in ethyl acetate (EtOAc) and the solution was dried over MgSO4. The solution was filtered and the solvent removed on a rotary evaporator. Purification by column chromatography on silica gel (400 g) using a gradient of 15-40% ethyl acetate in hexanes resulted in a isolation of the product as a yellow solid (18.0 g, 60%).

Quelle