Reaction #90844

Reaction equation

benzoquinone

acetic anhydride

sulfuric acid

water

→

triacetate

Conditions

Workup

1. 1
   Extractionextracting with dichloromethane (3×20 ml)
2. 2
   WashThe combined organics were washed with bicarbonate solution (3×50 ml), water (100 ml)
3. 3
   Dryingdried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   Otherevaporated

Procedure

The benzoquinone (4) (2 g) was dissolved in acetic anhydride (5 ml) and concentrated sulfuric acid (0.5 ml) was added slowly. The mixture was stirred in the dark at a temperature of 32° C. and monitored by HPLC. After a period of time of 44 h, the reaction was worked up by pouring into iced water (50 ml) and extracting with dichloromethane (3×20 ml). The combined organics were washed with bicarbonate solution (3×50 ml), water (100 ml), dried (MgSO4), filtered and evaporated to yield triacetate (5) which solidified (1.78 g).

Source