Reaction #531810

Reaction equation

HCl

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

NaOH

methanol

→

8b

Yield 74.0%

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

Yield 74.0%

Solvents

water

Conditions

Workup

1. 1
   TemperatureThe reaction was refluxed under Ar for 7 h
2. 2
   OtherAfter placing in an ice bath
3. 3
   Otherto give a yellow precipitate that
4. 4
   Filtrationwas filtered
5. 5
   Washwashed with water
6. 6
   Otherrecrystallized from THF/hexanes

Procedure

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