Reacción #48190

Ecuación de reacción

4-benzyloxy-3,5-dichloro-benzoic acid methyl ester

lithium aluminium hydride

→

(4-Benzyloxy-3,5-dichloro-phenyl)-methanol

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrocarefully quenched by addition of 2N sodium hydroxide solution in water
2. 2
   workup.STIRRINGAfter 20 minutes stirring the colour of the mixture
3. 3
   FiltraciónThe white precipitate was filtered off
4. 4
   Secadothe filtrate was dried over sodium sulphate
5. 5
   Concentraciónconcentrated under reduced pressure
6. 6
   OtroThe residue was recrystallised from dichloromethane/hexane

Procedimiento

A solution of 4-benzyloxy-3,5-dichloro-benzoic acid methyl ester (CAB02115, 7.20 g, 23.14 mmol) in THF (20 mL) was added slowly with a syringe to a suspension of lithium aluminium hydride (1.50 g, 39.5 mmol) in THF (40 mL). The reaction mixture was stirred for 30 minutes at room temperature and then carefully quenched by addition of 2N sodium hydroxide solution in water. After 20 minutes stirring the colour of the mixture turned from grey to white. The white precipitate was filtered off, the filtrate was dried over sodium sulphate and concentrated under reduced pressure. The residue was recrystallised from dichloromethane/hexane. Yield: 5.83 g (89%) white powder. 1H-NMR (400 MHz, CDCl3) δ 1.85 (t, J=5.9 Hz, 1H, —OH), 4.63 (d, J=5.9 Hz, 2H), 5.04 (s; 2H), 7.33 (s, 2H), 7.35-7.44 (m, 3H), 7.55-7.59 (m, 2H). 13C-NMR (100 MHz, CDCl3) δ=64.05, 75.03, 127.36, 128.70, 128.75, 129.91, 136.39, 138.64, 150.32.

Fuente