Reacción #531810

Ecuación de reacción

HCl

4-Acetyl-4′-benzyloxy-2′-methoxybiphenyl-2-carboxylic acid methyl ester

NaOH

methanol

→

8b

Rendimiento 74.0%

4-Acetyl-4′-benzyloxy-2′-methoxybiphenyl-2-carboxylic acid

Rendimiento 74.0%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction was refluxed under Ar for 7 h
2. 2
   OtroAfter placing in an ice bath
3. 3
   Otroto give a yellow precipitate that
4. 4
   Filtraciónwas filtered
5. 5
   Lavadowashed with water
6. 6
   Otrorecrystallized from THF/hexanes

Procedimiento

To 4-Acetyl-4′-benzyloxy-2′-methoxybiphenyl-2-carboxylic acid methyl ester 7b (4.06 g, 9.7 mmol) and NaOH (0.773 g, 19.4 mmol) was added methanol (60 mL) and water (60 mL). The reaction was refluxed under Ar for 7 h then cooled to room temperature. After placing in an ice bath, 1 M HCl was added to give a yellow precipitate that was filtered, washed with water and recrystallized from THF/hexanes to give 2.7 g (69%) of 8b as yellow crystals. 1H-NMR (400 MHz, CDCl3) dH 2.68 (4H, s, COCH3), 3.62 (3H, s, OCH3), 5.16 (2H, s, CH2Ph), 6.77 (1H, s, ArH), 7.18 (1H, s, ArH), 7.33-7.52 (5H, m, CH2Ph), 3.90 (3H, s, OCH3), 5.22 (2H, S, CH2Ph), 6.58 (1H, s, ArH), 6.90 (1H, s, ArH), 7.34-7.50 (6H, m, ArH+Ch2Ph), 8.17 (1H, d, ArH), 8.50 (1H, s, ArH),

Fuente