Dimethyl Sulfoxide → 8,8-Diphenyl-7-octenoic acid

HRID 1651219Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1651219
[H-].[Na+].CS(C)=O.[Br-].[C:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:10])=[O:9].[C:36]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)(=O)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>O1CCCC1>[C:37]1([C:36]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[CH:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:8]([OH:10])=[O:9])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 3102BenzophenoneHCID 24758Sodium hydrideHCID 11027094(6-Carboxyhexyl)triphenylphosphonium bromide

Produkt 1

HCID 145472218,8-Diphenyl-7-octenoic acidAusbeute 70,5 %

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; 8.36 g); dimethylsulfoxide (100 mL), (6-carboxyhexyl)triphenylphosphonium bromide (37.7 g), benzophenone (17.5 g); and tetrahydrofuran (100 mL). The crude product, isolated in the usual way, was recrystallized from hexane (200 mL) to yield 16.6 g of 8,8-diphenyl-7-octenoic acid, mp 88°-89° C. Anal. Calculated for C20H22O2 : C, 81.60; H, 7.53. Found: C, 81.34; H, 7.25.

Aufarbeitung

  1. customThe crude product, isolated in the usual way
  2. customwas recrystallized from hexane (200 mL)

Quellen und Nachweise

ORD-Eintrag
ord-1d22532ed7a14e08adc4c64b4915f69e
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04927838

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