Reaktion #531810

Reaktionsgleichung

HCl

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

NaOH

methanol

→

8b

Ausbeute 74.0%

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

Ausbeute 74.0%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was refluxed under Ar for 7 h
2. 2
   SonstigeAfter placing in an ice bath
3. 3
   Sonstigeto give a yellow precipitate that
4. 4
   Filtrationwas filtered
5. 5
   Waschenwashed with water
6. 6
   Sonstigerecrystallized from THF/hexanes

Vorschrift

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),

Quelle