Hydrochloric Acid → gamma-(9,10-Dihydro-9,10-methano-9-anthryl)-beta-butenoic acid

HRID 27964

Reaktionsgleichung

Reaktionsgleichung von HRID 27964
C([C:3]12[CH2:17][CH:10]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=31)[C:9]1[C:4]2=[CH:5][CH:6]=[CH:7][CH:8]=1)=O.[Cl-].[C:19]([CH2:22][CH2:23][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:21])=[O:20].[H-].[Na+].Cl.[CH3:46]S(C)=O>O1CCCC1.O>[CH:15]1[C:16]2[C:3]3([CH:46]=[CH:23][CH2:22][C:19]([OH:21])=[O:20])[CH2:17][CH:10]([C:9]4[C:8]3=[CH:7][CH:6]=[CH:5][CH:4]=4)[C:11]=2[CH:12]=[CH:13][CH:14]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 10270534(2-Carboxyethyl)triphenylphosphonium chlorideHCID 124041419,10-Methanoanthracene-9(10H)-carbaldehyde

Produkt 1

HCID 54474651gamma-(9,10-Dihydro-9,10-methano-9-anthryl)-beta-butenoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a mixture of 9-formyl-9,10-dihydro-9,10-methanoanthracene (110 mg) and β-carboxyethyltriphenylphosphonium chloride (186 mg) in dimethylsulfoxide (2 ml) and tetrahydrofuran (2 ml) was added 65.4% sodium hydride dispersion in mineral oil (37 mg) at 0° C. under nitrogen. The reaction mixture was stirred at 0° C. for 6 hours, diluted with water, acidified with hydrochloric acid and extracted with benzene. The benzene extract was shaken with 2 N aqueous sodium hydroxide. The basic layer was acidified with hydrochloric acid and extracted with ethyl acetate. The ethyl acetate extract was washed with water, dried over anhydrous sodium sulfate and evaporated to dryness to give γ-(9,10-dihydro-9,10-methano-9-anthryl)-β-butenoic acid. M.P. 166°-167° C.

Aufarbeitung

  1. extractionextracted with benzene
  2. extractionThe benzene extract
  3. stirringwas shaken with 2 N aqueous sodium hydroxide
  4. extractionextracted with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. washwas washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-6a1bcab99e7646dca3cfbb7012c89a4b
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04224344

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