Tetrahydrofuran → Benzoic acid, 4-hexyl-, methyl ester

HRID 1795375

Reaktionsgleichung

Reaktionsgleichung von HRID 1795375
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7](Cl)=[CH:6][CH:5]=1.C1COCC1.[CH2:17]([Mg]Br)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>CN1CCCC1=O>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 14307Methyl 4-chlorobenzoateHCID 178444609HCID 178444609, Verbindung

Produkt 1

HCID 591633Benzoic acid, 4-hexyl-, methyl esterAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

A flame-dried two-necked flask is charged under argon with 4-chlorobenzoic acid methyl ester (0.5 g, 2.93 mmol), FeCl2 (19 mg, 0.15 mmol), THF (7 mL) and N-methylpyrrolidone (NMP, 1 mL). A solution of n-hexylmagnesium bromide (2M in Et2O, 1.9 mL, 3.8 mmol) is added via syringe to the resulting red solution, causing an immediate color change to dark brown and finally to violet. The resulting mixture is stirred for 5 min. Work-up as described above provides 4-hexylbenzoic acid methyl ester as a colorless syrup (90%). The spectroscopic and analytical data are identical to those compiled above.

Quellen und Nachweise

ORD-Eintrag
ord-c06d75318af34b4e8de8eb8da5585337
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07026478B2

Verknüpfte Notizen

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