Benzyl Alcohol → Benzyl 4-bromo-2-methylbenzoate

HRID 24156

Reaktionsgleichung

Reaktionsgleichung von HRID 24156
[CH3:1][C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:12](O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N1C=CC=CC=1>O=S(Cl)Cl>[Br:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([O:6][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:5])=[C:2]([CH3:1])[CH:10]=1

Komponenten

5

Edukt 3

HCID 244Benzyl AlcoholHCID 1049PyridineHCID 995704-Bromo-2-methylbenzoic acid

Produkt 1

HCID 22568915Benzyl 4-bromo-2-methylbenzoateAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

Using General Esterification Method C; 2-methyl-4-bromo-benzoic acid (2.15 g, 10.0 mmols) was refluxed for 3 h with 10 mL SOCl2. The resulting solution concentrated under reduced pressure and the crude acyl chloride was combined with benzyl alcohol (1.08 g, 10.0 mmols) and pyridine (1.6 mL, 20.0 mmols) to give the title compound (2.4 g, 80%) after work-up and column chromatography (2-5% EtOAc—hexanes) as a colorless oil.

Aufarbeitung

  1. concentrationThe resulting solution concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5de0a88c24604da7b67995b4dbd98c81
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855512B2

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