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Benzyl Bromide → Benzyl 2-Benzylacrylate

HRID 36375
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 36375
[CH2:1]=[C:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(OCC)(=O)C>CN(C)C=O>[CH2:1]=[C:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([O:5][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:4]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 3035712-Benzylacrylic Acid

Produkt 1

HCID 10912012Benzyl 2-BenzylacrylateAusbeute 60,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The title acid of Step 9 (5.2 g, 30 mmol) was dissolved in dimethylformamide (25 mL) and cooled to 0° C. To this solution potassium carbonate (5.7 g, 41.48 mmol) was added followed by benzyl bromide (5.7 g, 29.7 mmol). The mixture was stirred at room temperature overnight. The mixture was filtered and the filtrate was diluted with ethyl acetate, washed with 3 times of water, brine. The solution was dried (Na2SO4) and evaporated. The residue was purified by flash chromotography on silica gel, eluting with 90:10 heptane:ethyl acetate to give the pure title compound as colorless oil (4.5 g, 60% yield). 1H NMR: 300 MHz spectrum consistent with proposed structure. Anal: calcd. for C17H16O2 : C, 80.93; H, 6.39. Found: C, 80.69; H, 6.47.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. additionthe filtrate was diluted with ethyl acetate
  3. washwashed with 3 times of water, brine
  4. dry with materialThe solution was dried (Na2SO4)
  5. customevaporated
  6. customThe residue was purified by flash chromotography on silica gel
  7. washeluting with 90:10 heptane

Quellen und Nachweise

ORD-Eintrag
ord-2d79bf1e031f404cbd4495a86c976c85
Quelldatensatz
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05414018

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