Reaktion #733986

ord-b4699f21b8784e2f809a670e97770a2b

Reaktionsgleichung

CC(C)Cc1ccc(C(C)(CCCCC(=O)CCCCC(C)(C(=O)O)c2ccc(CC(C)C)cc2)C(=O)O)cc1
210f
CC(C)Cc1ccc(C(C)(CCCCC(=O)CCCCC(C)(C(=O)O)c2ccc(CC(C)C)cc2)C(=O)O)cc1
2,12-Bis-(4-isobutylphenyl)-2,12-dimethyl-7-oxotridecanedioic acid
[K+].[OH-]
KOH
→
CC(C)(CCCCC(=O)CCCCC(C)(C)C(=O)O)C(=O)O
210c
Ausbeute 86.0%
CC(C)(CCCCC(=O)CCCCC(C)(C)C(=O)O)C(=O)O
7-Oxo-2,2,12,12-tetramethyltridecanedioic acid
Ausbeute 86.0%

Edukte

CC(C)Cc1ccc(C(C)(CCCCC(=O)CCCCC(C)(C(=O)O)c2ccc(CC(C)C)cc2)C(=O)O)cc1
210f
CC(C)Cc1ccc(C(C)(CCCCC(=O)CCCCC(C)(C(=O)O)c2ccc(CC(C)C)cc2)C(=O)O)cc1
2,12-Bis-(4-isobutylphenyl)-2,12-dimethyl-7-oxotridecanedioic acid
—
209c
[K+].[OH-]
KOH

Reagenzien

Keine

Lösungsmittel

CCO
ethanol
O
water

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturat reflux for 5 h
  2. 2
    SonstigeThe solid product obtained
  3. 3
    Extraktionafter extraction
  4. 4
    Sonstigedrying
  5. 5
    Sonstigewas purified by flash chromatography (silica; hexanes/ethyl acetate=90/10)

Vorschrift

According to the procedure given for 210f, 209c (30.0 g, 81.0 mmol) was saponified with KOH (85%, 18.9 g, 286 mmol) in ethanol (143 mL) and water (48 mL) at reflux for 5 h. The solid product obtained after extraction and drying was purified by flash chromatography (silica; hexanes/ethyl acetate=90/10) to afford 210c (22.0 g, 86%) as a white solid. Mp 60-61.5° C. 1H NMR (CDCl3): δ 11.40 (br., 2H), 2.41 (t, 4H, J=7.3), 1.62-1.48 (m, 8H), 1.32-1.18 (m, 4H), 1.18 (s, 12H). 13C NMR (CDCl3=77.0 ppm): δ 211.11, 184.74, 42.49, 42.14, 40.42, 24.92, 24.62, 23.99. HRMS (LSIMS, gly): Calcd for C17H31O5 (MH+): 315.2171, found: 315.2183. HPLC: 94.5% pure. Anal. (C17H30O5) C, H.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07705177B2uspto-grants-2010_04