Ethyl Acetate → 5-(9-Methoxycarbonyl-nonyloxy)-isophthalic Acid Di-tert-butyl Ester

HRID 1022416Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1022416
[C:1]([O:5][C:6](=[O:21])[C:7]1[CH2:8][C:9](O)([CH:17]=[CH:18][CH:19]=1)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=[O:23].[K+].[K+].Br[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([O:40][CH3:41])=[O:39].CCOC(C)=O>CC(C)=O.O>[C:1]([O:5][C:6](=[O:21])[C:7]1[CH:19]=[C:18]([O:23][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([O:40][CH3:41])=[O:39])[CH:17]=[C:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium Carbonate3×HCID 554079Methyl 10-bromodecanoate2×HCID 684422113-Hydroxy-isophthalic Acid Di-tert-butyl Ester

Produkt 1

HCID 684414955-(9-Methoxycarbonyl-nonyloxy)-isophthalic Acid Di-tert-butyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

3-Hydroxy-isophthalic acid di-tert-butyl ester (90 mg, 0.3 mmol) was dissolved in dry acetone (5 ml), K2CO3 (90 mg, 0.65 mmol) and methyl 10-bromodecanoate (0.075 ml, 0.3 mmol) was added. The mixture was heated to reflux. The heating caused dissolution of the K2CO3. After a while, a precipitate was formed. Reflux (50° C.) was continued over night. More K2CO3 (30 mg, 0.2 mmol) and methyl 10-bromodecanoate (0.025 ml, 0.1 mmol) was added. The mixture was refluxed at 50° C. over night. To the dry reaction mixture EtOAc and water was added. After extraction, the organic layer was washed with water and brine, dried (Na2SO4) and concentrated to give the crude title compound as a clear oil.

Aufarbeitung

  1. temperatureThe mixture was heated to reflux
  2. customAfter a while, a precipitate was formed
  3. waitwas continued over night
  4. temperatureThe mixture was refluxed at 50° C. over night
  5. additionwas added
  6. extractionAfter extraction
  7. washthe organic layer was washed with water and brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8fa3a90c8c5245e097778c80c620e377
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722620B2

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