Reacción #1772042

Ecuación de reacción

(E)-5-(3-Bromophenyl)pent-4-enoic acid

→

5-(3-bromophenyl)pentanoic acid

Rendimiento 99.0%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroflushed with nitrogen before addition of 5% platinum sulfide on carbon (2.5 g)
2. 2
   OtroThe solution was flushed with hydrogen at atmospheric pressure
3. 3
   OtroThe catalyst was removed by filtration through diatomaceous earth (Celite®)
4. 4
   Otrothe solvent immediately removed by rotory evaporation (in order to minimized esterification)

Procedimiento

Example 1, (E)-5-(3-Bromophenyl)pent-4-enoic acid (4 g, 15.8 mmol), was dissolved in absolute ethanol (200 mL) and flushed with nitrogen before addition of 5% platinum sulfide on carbon (2.5 g). The solution was flushed with hydrogen at atmospheric pressure and stirred 5 hours. The catalyst was removed by filtration through diatomaceous earth (Celite®) and the solvent immediately removed by rotory evaporation (in order to minimized esterification) to give Example 2, 5-(3-bromophenyl)pentanoic acid 4 g (99%) which was carried forward without further purification. 1H NMR (500 MHz, CDCl3) δ 7.31-7.30 (m, 2H), 7.13 (t, J=7.6 Hz, 1H), 7.09-7.07 (d, J=7.6 Hz, 1H), 2.60 (t, J=7.0 Hz, 2H), 2.37 (t, J=7.0 Hz, 2H), 1.68-1.65 (m, 4H). RT=2.1 minutes (condition 1); LRMS: Anal. Calcd. for C11H13BrO2: 255.00. found: 254.99 (M−H).

Fuente