Dimethyl Sulfoxide → 6,6-Diphenylhex-5-enoic acid

HRID 1651217

Reaktionsgleichung

Reaktionsgleichung von HRID 1651217
[H-].[Na+].CS(C)=O.[Br-].[C:8]([CH2:11][CH2:12][CH2:13][CH2:14][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:10])=[O:9].[C:34]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)(=O)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>O1CCCC1>[C:35]1([C:34]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[CH:14][CH2:13][CH2:12][CH2:11][C:8]([OH:10])=[O:9])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 3102BenzophenoneHCID 24758Sodium hydrideHCID 161236(4-Carboxybutyl)triphenylphosphonium bromide

Produkt 1

HCID 43746276,6-Diphenylhex-5-enoic acidAusbeute 75,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The reaction was carried out as in Example 87 using the following reagents: sodium hydride (56% dispersion in oil; 8.6 g), dimethylsulfoxide (100 mL), (4-carboxybutyl)triphenylphosphonium bromide (36.5 g), benzophenone (18.2 g), and tetrahydrofuran (100 mL). The crude product, isolated in the usual manner, was crystallized from hexane to give 16.5 g of 6,6-diphenyl-5-hexenoic acid, mp 111°-112.5° C. Anal. Calculated for C18H18O2 : C, 81.17; H, 6.81. Found: C, 81.39; H, 6.88.

Aufarbeitung

  1. customThe crude product, isolated in the usual manner
  2. customwas crystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-f3444ea693ce4d0e8b82023a7223aecf
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04927838

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