Réaction #531810

Équation de réaction

HCl

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

NaOH

methanol

→

8b

Rendement 74.0%

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

Rendement 74.0%

Solvants

water

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction was refluxed under Ar for 7 h
2. 2
   AutreAfter placing in an ice bath
3. 3
   Autreto give a yellow precipitate that
4. 4
   Filtrationwas filtered
5. 5
   Lavagewashed with water
6. 6
   Autrerecrystallized from THF/hexanes

Mode opératoire

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),

Source