Styrene → (s)-2-Phenylpropanal

HRID 261000

Reaktionsgleichung

Reaktionsgleichung von HRID 261000
C=CC1C=CC=CC=1.[H][H].[C]=O.C1(CC2C=CC=CC=2)C=CC=CC=1.[C:26]1([CH:32]([CH3:35])[CH:33]=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C1(CCC=O)C=CC=CC=1>C1C=CC=CC=1>[C:26]1([C@H:32]([CH3:35])[CH:33]=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Komponenten

7

Edukt 5

HCID 7501Styrene2×HCID 7580DiphenylmethaneHCID 867495872-Phenylpropanal 3-phenylpropanalHCID 178418361HCID 178418361, VerbindungHCID 178418416HCID 178418416, Verbindung

Produkt 1

HCID 5478986(s)-2-Phenylpropanal

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

In a 50 ml autoclave were charged 38.7 mg (0.0488 mmol) of (S,R)-biphemphos, 3.1 mg (0.012 mmol) of Rh(acac)(CO)2, and a solution of 1250 mg (12.0 mmol) of styrene in 2.4 ml of benzene, and hydrogen and carbon monoxide were fed thereto each to a partial pressure of 50 atm. The mixture was stirred at 60° C. for 42 hours. A conversion of the starting olefin and an aldehyde production ratio were determined by 1H-NMR (internal standard: diphenylmethane) analysis, and an optical purity (enantiomer excess) was determined by GLC analysis after conversion of the resulting optically active aldehyde into the corresponding carboxylic acid by Jones oxidation. As a result, the conversion of styrene was 100%, and the 2-phenylpropanal/3-phenylpropanal production ratio was 9:1. The 2-phenylpropanal produced had an optical purity of (S)-(+)-2-phenylpropanal of 94% ee.

Quellen und Nachweise

ORD-Eintrag
ord-b2c95705e9884479b4067b9908d5ba74
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05530150

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