Benzyl Bromide → 4-Pentenoic acid, phenylmethyl ester

HRID 707669

Reaktionsgleichung

Reaktionsgleichung von HRID 707669
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([OH:15])(=[O:14])[CH2:10][CH2:11][CH:12]=[CH2:13].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([O:15][C:9](=[O:14])[CH2:10][CH2:11][CH:12]=[CH2:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 611384-Pentenoic acid

Produkt 1

HCID 100520354-Pentenoic acid, phenylmethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 180AcetoneLösungsmittel

Versuchsvorschrift

Benzyl bromide (7.19 g, 42.04 mmol) was added to a solution of 4-pentenoic acid (6) (5.05 g, 50.45 mmol, 1.2 eq.) in acetone (75 ml) at RT under N2. Anhydrous potassium carbonate (29.05 g, 210.19 mmol, 5.0 eq.) and tetrabutylammonium iodide (0.776 g, 2.102 mmol, 0.05 eq.) were added and the resulting suspension was stirred over 2 days. LCMS analysis showed mainly product.

Quellen und Nachweise

ORD-Eintrag
ord-439d5aef3c3846a581ca6f50f0f9aee2
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09175032B2

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