Formaldehyde → 3-Phenoxyprop-2-enal

HRID 2105629

Reaktionsgleichung

Reaktionsgleichung von HRID 2105629
[O:1]([CH2:8][CH:9]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.Cl.C(N[CH2:17][CH3:18])C.[CH2:19]([O:21]P([CH2:27][C:28]([OH:30])=[O:29])(OCC)=O)C.C([Li])CCC>O1CCCC1.CCOCC>[C:2]1([O:1][CH:8]=[CH:9][CH:19]=[O:21])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[O:1]([CH:8]=[CH:17][CH:18]=[CH:27][C:28]([OH:30])=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

9

Edukt 5

HCID 712FormaldehydeHCID 36704(Diethoxyphosphinyl)acetic acidHCID 75033PhenoxyacetaldehydeHCID 10197650Diethylammonium chlorideHCID 178418339Butyllithium

Produkt 2

HCID 543072073-Phenoxyprop-2-enalHCID 738633705-Phenoxy-2,4-pentadienoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-Formylvinyl phenyl ether is prepared by treating phenoxyacetaldehyde with formaldehyde and diethylamine hydrochloride salt. The ether is then reacting with a solution of diethylphosphonoacetic acid and n-butyllithium in anhydrous tetrahydrofuran (THF) to form 5-phenoxy-2,4-pentadienoic acid. 5-Phenyl-2,4-pentadienal is obtained by first converting the carboxylic acid to a Weinreb amide using oxalyl chloride followed by N,O-dimethylhydroxylamine. Subsequently, reduction of the Weinreb amide with lithium aluminum hydride (LAH) in THF leads to the formation of 5-phenoxy-2,4-pentadienal. The synthesis is summarized in Scheme II.

Quellen und Nachweise

ORD-Eintrag
ord-760afae2ebd147e1985a5c120b3f69f7
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07579372B2

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