4-Propoxybenzaldehyde → 6-(p-Propoxyphenyl)-5-hexenoic acid

HRID 610684

Reaktionsgleichung

Reaktionsgleichung von HRID 610684
[Br-].[C:2]([CH2:5][CH2:6][CH2:7][CH2:8][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:4])=[O:3].[CH2:28]([O:31][C:32]1[CH:39]=[CH:38][C:35]([CH:36]=O)=[CH:34][CH:33]=1)[CH2:29][CH3:30]>C1COCC1>[CH2:28]([O:31][C:32]1[CH:39]=[CH:38][C:35]([CH:36]=[CH:8][CH2:7][CH2:6][CH2:5][C:2]([OH:4])=[O:3])=[CH:34][CH:33]=1)[CH2:29][CH3:30]

Komponenten

4

Edukt 2

HCID 798124-PropoxybenzaldehydeHCID 161236(4-Carboxybutyl)triphenylphosphonium bromide

Produkt 1

HCID 540403946-(p-Propoxyphenyl)-5-hexenoic acidAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

This compound was synthesized from 4-carboxybutyltriphenylphosphonium bromide (8.87 g, 20 mmol) and p-propoxybenzaldehyde (3.28 g, 20 mmol, synthesized from p-hydroxybenzaldehyde and 1-iodopropane) in THF (100 mL) by a Wittig reaction. Crystallization (petroleum ether) afforded the product (3.75 g, 76%) as white crystals (mp, 49-50° C.). IR: 3400-2500, 1725 cm-1 ; 1H-NMR: 1.00 (t, 3), 1.75 (m, 4H), 2.35 (m, 4H), 3.90 (t, 2H), 5.55 (m, 1H), 6.35 (m, 1H), 7.00 (q, 4H), 11.30 (bs, 1H). Anal. Calcd. for C15H20O3 : C, 72.55, H, 8.12%; Found: C, 72.45, H, 8.13%. Z:E=35:65.

Aufarbeitung

  1. customCrystallization (petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-cd8ff5cdabd9442286a3a3ac8c5393af
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998642

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