HCID 69949538, Verbindung → 4-CarboxyMethyl-cyclohexanecarboxylic acid ethyl ester

HRID 2298965Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2298965
[C:1]([O:5][C:6]([CH:8]1[CH2:13][CH2:12][C:11](=[CH:14][C:15]([O:17]C(C)(C)C)=[O:16])[CH2:10][CH2:9]1)=[O:7])(C)(C)[CH3:2].[H][H]>[Pd].C(O)C>[CH2:1]([O:5][C:6]([CH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([OH:17])=[O:16])[CH2:10][CH2:9]1)=[O:7])[CH3:2]

Komponenten

5

Edukt 2

HCID 69949538HCID 69949538, VerbindungHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 158961924-CarboxyMethyl-cyclohexanecarboxylic acid ethyl esterAusbeute 99,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of diester (B) (12.5 g, 46.3 mmol) and 10% palladium on activated carbon (5 g) in absolute ethanol (200 mL) was exposed to a hydrogen atmosphere (at balloon pressure) and stirred vigorously for 1 h. After removal of catalyst by filtration and concentration, the resultant colorless oil was dissolved in methylene chloride (150 mL) and TFA (75 mL) and stirred for 15 min. All volatiles were removed by rotary evaporation and the resultant colorless oil placed under high vacuum to give (C) 4-carboxymethyl-cyclohexanecarboxylic acid ethyl ester (9.9 g, 99%) as a white solid. Data for cis/trans mixture: 1H NMR (400 MHz, CD3OD) δ4.13 (2q, 4 H), 2.58 (m, 1H), 2.30-2.20 (m, 1 H), 2.20 (2d, 4 H), 2.05-1.80 (m, 7 H), 1.80-1.55 (m, 5 H), 1.50-1.38 (m, 3 H), 1.32-1.25 (m, 1 H), 1.25 (2t, 6 H), 1.10-1.00 (m, 2 H); mass spectrum m/z 215 [(M+H)+; calcd for C11H19O4: 215].

Aufarbeitung

  1. customAfter removal of catalyst
  2. filtrationby filtration and concentration
  3. dissolutionthe resultant colorless oil was dissolved in methylene chloride (150 mL)
  4. stirringTFA (75 mL) and stirred for 15 min
  5. customAll volatiles were removed by rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-4eae9c3e84fc40fb8eb38ab3fffa9aa5
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06495561B2

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