Reaktion #733989

Reaktionsgleichung

210f

2,12-Bis-(4-isobutylphenyl)-2,12-dimethyl-7-oxotridecanedioic acid

209g

2,2,14,14-Tetramethyl-8-oxopentadecanedioic acid diethyl ester

KOH

→

210g

Ausbeute 57.0%

2,2,14,14-Tetramethyl-8-oxopentadecanedioic acid

Ausbeute 57.0%

Lösungsmittel

ethanol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux for 4 h
2. 2
   SonstigeThe solid product obtained after usual workup
3. 3
   Sonstigewas recrystallized from Et2O/hexanes (50 mL/50 mL)

Vorschrift

According to the procedure given for 210f, 209g (8.54 g, 21.4 mmol) was saponified with KOH (85%, 4.53 g, 68.6 mmol) in ethanol (13 mL) and water (5 mL) at reflux for 4 h. The solid product obtained after usual workup was recrystallized from Et2O/hexanes (50 mL/50 mL), affording 210g (4.16 g, 57%) as colorless needles. Mp 82-83° C. 1H NMR (CDCl3): δ 11.53 (br., 2H), 2.39 (t, 4H, J=7.3), 1.60-1.50 (m, 8H), 1.30-1.20 (m, 8H), 1.18 (s, 12H). 13C NMR (CDCl3): δ 211.7, 185.0, 42.8, 42.3, 40.4, 29.7, 25.1, 24.8, 23.8. HRMS (LSIMS, gly): Calcd for C19H31O5 (MH+): 343.2484, found: 343.2444. HPLC: 92.6% pure. Anal. (C19H34O5) C, H.

Quelle