tert-Butanol → 1-(1,1-Dimethylethyl) 6-methyl hexanedioate

HRID 331539

Reaktionsgleichung

Reaktionsgleichung von HRID 331539
[CH3:1][O:2][C:3](=[O:11])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9].C1N=CN(C(N2C=NC=C2)=O)C=1.[C:24](O)([CH3:27])([CH3:26])[CH3:25].C1CCN2C(=NCCC2)CC1>CN(C=O)C.CCOCC>[CH3:1][O:2][C:3](=[O:11])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:9]

Komponenten

7

Edukt 4

HCID 6386tert-ButanolHCID 12328monoMethyl adipateHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Produkt 1

HCID 184750351-(1,1-Dimethylethyl) 6-methyl hexanedioateAusbeute 78,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of adipic acid monomethyl ester (4.8 g, 30 mmol) in DMF (30 mL), was added CDI (4.9 g, 30 mmol), and the resulting mixture was stirred under N2 at 40° C. for 1 hour. t-Butanol (4.4 g, 60 mmol) and DBU (4.6 g, 30 mmol) were added, and stirring proceeded at 40° C. for 70 hours. The mixture was poured into ether (100 mL), and this mixture was washed with 10% aq. HOAc (100 mL), 10% aq. K2CO3 (100 mL), and water (3×100 mL), dried (MgSO4), and evaporated, providing 5.1 g of hexanedioic acid tert-butyl ester methyl ester, in 78% yield; 1H NMR (CDCl3) δ 1.44 (s, 9H), 1.59-1.67 (m, 4H), 2.21-2.26 (m, 2H), 3.67 (s, 3H).

Aufarbeitung

  1. stirringstirring
  2. waitproceeded at 40° C. for 70 hours
  3. washthis mixture was washed with 10% aq. HOAc (100 mL), 10% aq. K2CO3 (100 mL), and water (3×100 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-36512b5498e647e7b4a520a5f9e50622
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877780B2

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