Allyl bromide → 6-Allyloxy-4-ethyl-3-methyl-phthalic Acid Dimethyl Ester

HRID 540713Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 540713
[CH3:1][O:2][C:3](=[O:18])[C:4]1[C:5](=[C:10]([CH3:17])[C:11]([CH2:15][CH3:16])=[CH:12][C:13]=1[OH:14])[C:6]([O:8][CH3:9])=[O:7].C(=O)([O-])[O-].[K+].[K+].[CH2:25](Br)[CH:26]=[CH2:27]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:18])[C:4]1[C:5](=[C:10]([CH3:17])[C:11]([CH2:15][CH3:16])=[CH:12][C:13]=1[O:14][CH2:27][CH:26]=[CH2:25])[C:6]([O:8][CH3:9])=[O:7]

Komponenten

5

Edukt 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 597944774-Ethyl-6-hydroxy-3-methyl-phthalic Acid Dimethyl Ester

Produkt 1

HCID 574598616-Allyloxy-4-ethyl-3-methyl-phthalic Acid Dimethyl EsterAusbeute 83,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

4-Ethyl-6-hydroxy-3-methyl-phthalic acid dimethyl ester (1.01 g, 4.02 mmol) was dissolved in DMF (5 mL). Potassium carbonate (3.33 g, 24.14 mmol) was added, followed by allylbromide (2.92 g, 24.14 mmol). The suspension was heated at 60° C. After 14 hrs, the reaction was cooled to room temperature and filtered. The solvents were removed in vacuo and the crude material was purified by silica gel chromatography to provide 0.976 g (83%) of the desired product as a colorless oil. 1H NMR (300 MHz, CDCl3): δ=1.16 (t, J=7.2 Hz, 3H), 2.20 (s, 3H), 2.62 (q, J=7.2 Hz, 2H), 3.83 (s, 3H), 3.84 (s, 3H), 4.57 (m, 2H), 5.26 (dd, J=9.3, 1.5 Hz, 1H), 5.41 (dd, J=13.5, 1.5 Hz, 1H), 5.98 (m, 1H), 6.82 (s, 1H) ppm.

Aufarbeitung

  1. temperaturethe reaction was cooled to room temperature
  2. filtrationfiltered
  3. customThe solvents were removed in vacuo
  4. customthe crude material was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-57978a0ccd2e4e15bc574bdd781a4cc7
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871785B2

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