6-Hydroxy-3-methyl-4-vinyl-phthalic Acid Dimethyl Ester → 4-Ethyl-6-hydroxy-3-methyl-phthalic Acid Dimethyl Ester

HRID 272194

Reaktionsgleichung

Reaktionsgleichung von HRID 272194
[CH3:1][O:2][C:3](=[O:18])[C:4]1[C:5](=[C:10]([CH3:17])[C:11]([CH:15]=[CH2:16])=[CH:12][C:13]=1[OH:14])[C:6]([O:8][CH3:9])=[O:7]>C1C=CC=CC=1.CCOC(C)=O>[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]

Komponenten

4

Edukt 1

HCID 597944986-Hydroxy-3-methyl-4-vinyl-phthalic Acid Dimethyl Ester

Produkt 1

HCID 597944774-Ethyl-6-hydroxy-3-methyl-phthalic Acid Dimethyl EsterAusbeute 88,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

6-Hydroxy-3-methyl-4-vinyl-phthalic acid dimethyl ester (1.27 g, 5.11 mmol) was dissolved in benzene (10 mL) and EtOAc (10 mL). Tristriphenylphosphine rhodium chloride (150 mg) was added and the reaction was placed under an atmosphere of hydrogen. Stirring at room temperature was continued. After 14 hours, the solvents were removed in vacuo and the crude material was purified by silica gel chromatography to provide 1.14 g (88%) of the desired product as an off-white solid. 1H NMR (300 MHz, CDCl3): δ=1.19 (t, J=7.8 Hz, 3H), 2.10 (s, 3H), 2.60 (q, J=7.8 Hz, 2H), 3.89 (s, 6H), 6.87 (s, 1H), 10.79 (s, 1H) ppm.

Aufarbeitung

  1. customthe solvents were removed in vacuo
  2. customthe crude material was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f030c0e328744626b6a9d1e4a949d794
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452901B2

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