Benzaldehyde → 12-Phenyl-11-dodecenoic acid

HRID 377488

Reaktionsgleichung

Reaktionsgleichung von HRID 377488
[Br-].[C:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:4])=[O:3].[CH:34](=O)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C1COCC1>[C:35]1([CH:34]=[CH:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:2]([OH:4])=[O:3])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Komponenten

4

Edukt 2

HCID 240BenzaldehydeHCID 11432504Phosphonium, (10-carboxydecyl)triphenyl-, bromide

Produkt 1

HCID 5453176312-Phenyl-11-dodecenoic acidAusbeute 44,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

This compound was synthesized from 10-carboxydecyltriphenylphosphonium bromide (10.55 g, 20 mmol) and benzaldehyde (2.12 g, 20 mmol) in THF (100 mL) by a Wittig reaction. Kugelrohr distillation (bp 152-155° C./0.03 torr) and crystallization afforded the product (2.43 g, 44%) as white crystals (mp 27-27.5° C.). IR: 3400-2500, 1720, 700 cm-1 ; 1H-NMR: 1.30 (m, 10H), 1.40 (m, 2H), 1.62 (m, 2H), 2.35 (m, 4H), 5.65 (m, 1H), 6.40 (m, 1H), 7.25 (m, 5H), 10.40 (bs, 1H). Anal. Calcd. for C18H26O2 : C, 78.79, H, 9.55%; Found: C, 78.66, H, 9.60%. Z:E=93:7.

Aufarbeitung

  1. distillationKugelrohr distillation (bp 152-155° C./0.03 torr) and crystallization

Quellen und Nachweise

ORD-Eintrag
ord-aca20dc80d0e4611ade9027c473c767f
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06025511

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