Benzyl Alcohol → Benzyl 2-bromopropanoate

HRID 1771025

Reaktionsgleichung

Reaktionsgleichung von HRID 1771025
[Br:1][CH:2]([CH3:6])[C:3]([OH:5])=[O:4].[CH2:7](O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1CCCCC1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][CH:2]([CH3:6])[C:3]([O:5][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]

Komponenten

5

Edukt 2

HCID 244Benzyl AlcoholHCID 117292-Bromopropionic acid

Produkt 1

HCID 298874Benzyl 2-bromopropanoateAusbeute 104,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 521998p-Toluenesulfonic acid monohydrateKatalysatorHCID 8078CyclohexaneLösungsmittel

Versuchsvorschrift

A mixture of 2-bromopropanoic acid (15.3 g; 100 mmol), benzyl alcohol (13.0 g; 120 mmol) and p-toluenesulphonic acid monohydrate (50 mg) in cyclohexane (200 mL) was refluxed in a Dean-Stark apparatus for 19 h. The reaction mixture was cooled to ambient temperature, washed with saturated NaHCO3 solution (1×30 mL), water (1×30 mL) and saturated NaCl solution (1×30 mL). After drying (MgSO4), filtration, and evaporation, the residue was vacuum-distilled. 25.4 g (87%) product was obtained (colourless liquid, by 111-113° C./1.1 mm Hg).

Aufarbeitung

  1. temperaturewas refluxed in a Dean-Stark apparatus for 19 h
  2. washwashed with saturated NaHCO3 solution (1×30 mL), water (1×30 mL) and saturated NaCl solution (1×30 mL)
  3. customAfter drying
  4. filtration(MgSO4), filtration, and evaporation
  5. distillationthe residue was vacuum-distilled

Quellen und Nachweise

ORD-Eintrag
ord-10a9ddd574304b13a83b02599ad4795f
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249086B2

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