Reaction #1375813

Reaction equation

methyl 4-tri-n-butylstannylbenzoate

KOH

acetic acid

water

→

title compound

Yield 90.3%

4-Tri-n-butylstannylbenzoic acid

Yield 90.3%

Solvents

ethanol

Conditions

Workup

1. 1
   TemperatureThe resulting solution was refluxed for 2 hours
2. 2
   TemperatureThe solution was cooled
3. 3
   ExtractionThe solution was then extracted with diethyl ether (80 ml)
4. 4
   WashThe ether phase was washed with water (30 ml)
5. 5
   Dryingdried over MgSO4 (5 g)
6. 6
   Filtrationfiltered
7. 7
   Otherevaporated under reduced pressure

Procedure

To a solution of methyl 4-tri-n-butylstannylbenzoate (3.0 g, 7 mmol) in absolute ethanol (60 ml) was added 0.25 g KOH (9 mmol). The resulting solution was refluxed for 2 hours. The solution was cooled and poured into an ice-cold solution of acetic acid (0.64 g, 10.6 mmol) and water (100 ml). The solution was then extracted with diethyl ether (80 ml). The ether phase was washed with water (30 ml), dried over MgSO4 (5 g), filtered and evaporated under reduced pressure to afford 2.6 g (88%) of the title compound. This material was used without further purification.

Source