Reaction #80926

Reaction equation

6-chloro-7-cyano-2,3-dihydro-2,2-dimethylbenzofuran

potassium hydroxide

water

→

7-aminocarbonyl-6-chloro-2,3-dihydro-2,2-dimethylbenzofuran

Yield 75.7%

Solvents

2-methyl-2-propanol

Conditions

Workup

1. 1
   Temperatureto reflux
2. 2
   workup.ADDITIONUpon completion of addition
3. 3
   Temperaturethe reaction mixture was heated
4. 4
   Temperatureat reflux for about 75 minutes
5. 5
   TemperatureThe reaction mixture was then cooled
6. 6
   Temperaturewas cooled in an ice bath
7. 7
   FiltrationThe resultant solid was collected by filtration
8. 8
   Otherdried under vacuum

Procedure

A stirred solution of 10.0 grams (0.048 mole) of 6-chloro-7-cyano-2,3-dihydro-2,2-dimethylbenzofuran in 200 mL of 2-methyl-2-propanol was warmed to reflux, and 9.5 grams (0.17 mole) of 85% potassium hydroxide was added in one portion. Upon completion of addition, the reaction mixture was heated at reflux for about 75 minutes. The reaction mixture was then cooled and poured into 400 mL of water that was cooled in an ice bath. The resultant solid was collected by filtration and dried under vacuum, yielding 8.2 grams of 7-aminocarbonyl-6-chloro-2,3-dihydro-2,2-dimethylbenzofuran. The NMR spectrum was consistent with the proposed structure.

Source