Acetaldehyde → Ethyl 3-(1-propenyl)benzoate

HRID 443664

Reaktionsgleichung

Reaktionsgleichung von HRID 443664
[Br-].[CH3:2][O:3][C:4]([C:6]1[CH:7]=[C:8]([CH:29]=[CH:30][CH:31]=1)[CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:5].[O-][CH2:33][CH3:34].[Na+].[CH:36](=O)C>C(O)C>[CH:9]([C:8]1[CH:7]=[C:6]([CH:31]=[CH:30][CH:29]=1)[C:4]([O:3][CH2:2][CH3:36])=[O:5])=[CH:33][CH3:34]

Komponenten

5

Edukt 3

HCID 177AcetaldehydeHCID 2723922Sodium ethoxideHCID 10051285Phosphonium, [[3-(methoxycarbonyl)phenyl]methyl]triphenyl-, bromide

Produkt 1

HCID 53648757Ethyl 3-(1-propenyl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

The preparation of XIII begins with the known methyl 3-(bromomethyl)benzoate. This halide is heated in xylene solution with triphenylphosphine to yield (3-methoxycarbonylbenzyl)triphenylphosphonium bromide. The phosphonium salt is converted to the ylide with sodium ethoxide in ethanol and the ylide caused to react with acetaldehyde to yield ethyl 3-(1-propenyl)benzoate. [Note that the ethyl ester has been obtained as a result of transesterification with solvent ethanol.] The ester is heated with N-bromosuccinimide in carbon tetrachloride for an extended period to yield ethyl 3-(3-bromo-1-propenyl)benzoate. This compound is treated with the anion derived from methyl methylthiomethyl sulfoxide as described in previous examples. The resulting dimethyl mercaptal S-oxide is hydrolyzed with acid catalysis to the aldehyde reagent XIII.

Quellen und Nachweise

ORD-Eintrag
ord-63a6c990653c49fb9aac1405afe3b12d
Quelldatensatz
uspto-grants-1981_04
Patentnummer
US04260771

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