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

HRID 47987
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 47987
C([O:3][C:4](=[O:44])[C:5]([C:34]1[CH:39]=[CH:38][C:37]([CH2:40][CH:41]([CH3:43])[CH3:42])=[CH:36][CH:35]=1)([CH3:33])[CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:32])[CH2:11][CH2:12][CH2:13][CH2:14][C:15]([C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH:29]([CH3:31])[CH3:30])=[CH:24][CH:23]=1)([CH3:21])[C:16]([O:18]CC)=[O:17])C.O.[OH-].[K+]>C(O)C>[CH2:28]([C:25]1[CH:24]=[CH:23][C:22]([C:15]([CH3:21])([CH2:14][CH2:13][CH2:12][CH2:11][C:10](=[O:32])[CH2:9][CH2:8][CH2:7][CH2:6][C:5]([C:34]2[CH:35]=[CH:36][C:37]([CH2:40][CH:41]([CH3:43])[CH3:42])=[CH:38][CH:39]=2)([CH3:33])[C:4]([OH:44])=[O:3])[C:16]([OH:18])=[O:17])=[CH:27][CH:26]=1)[CH:29]([CH3:31])[CH3:30]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 11410899Diethyl 2,12-bis(4-isobutylphenyl)-2,12-dimethyl-7-oxotridecanedioate

Produkt 1

HCID 103252762,12-Bis-(4-isobutylphenyl)-2,12-dimethyl-7-oxotridecanedioic acidAusbeute 86,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702Ethanol
Lösungsmittel

Versuchsvorschrift

2,12-Bis-(4-isobutyl-phenyl)-2,12-dimethyl-7-oxo-tridecanedioic acid diethyl ester (3.0 g, 4.95 mmol) was dissolved in ethanol (40 mL) and water (10 mL) with potassium hydroxide (4.4 g 85%). The solution was heated to reflux for six hours, cooled and concentrated. After the ethanol was removed, water (200 mL) was added and the solution was extracted with diethyl ether (100 mL). The aqueous fraction was acidified with concentrated hydrochloric acid (10 mL, to pH=1). The product was then extracted with diethyl ether (2×100 mL). The ether fractions were combined and dried with sodium sulfate (5 g). After filtration, concentration and drying under high vacuum, the reaction yielded 2,12-bis-(4-isobutyl-phenyl)-2,12-dimethyl-7-oxo-tridecanedioic acid (2.35 g, 82% yield) as a light yellow foam. 1H NMR (300 MHz, CDCl3/TMS): δ (ppm) 10.02 (bs, 2H), 7.24 (d, 4H, J=8.0 Hz), 7.09 (d, 4H, J=8.0 Hz), 2.43 (d, 4H, J=7.0 Hz), 2.33 (t, 4H, J=7.3 Hz), 2.05-1.88 (m, 2H), 1.96-1.77 (m, 4H), 1.55-1.42 (m, 10H), 1.22-1.08 (m, 4H), 0.88 (d, 12H, J=6.6). 13C NMR (75 MHz, CDCl3/TMS): δ (ppm): 211.48, 182.94, 140.43, 140.24, 129.27, 125.94, 49.71, 45.06, 42.58, 42.58, 38.91, 30.25, 24.45, 24.24, 22.58, 22.40. HRMS (LSIMS, nba): Calcd. for C35H50O5Na (MNa+): 573.3555, found: 573.3459.

Aufarbeitung

  1. temperatureThe solution was heated
  2. temperatureto reflux for six hours
  3. temperaturecooled
  4. concentrationconcentrated
  5. customAfter the ethanol was removed
  6. additionwater (200 mL) was added
  7. extractionthe solution was extracted with diethyl ether (100 mL)
  8. extractionThe product was then extracted with diethyl ether (2×100 mL)
  9. dry with materialdried with sodium sulfate (5 g)
  10. filtrationAfter filtration, concentration
  11. customdrying under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-6eabff3f43584dbd96fd1e1462fc9f9c
Quelldatensatz
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06699910B2

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