Catechol → Ethyl spiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-4'-carboxylate

HRID 2040298Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2040298
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.[C:13]1([C:15](=[CH:17][CH:18]=[CH:19][CH:20]=1)O)[OH:14].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)C>[C:2]12([O:14][C:13]3[CH:15]=[CH:17][CH:18]=[CH:19][C:20]=3[O:1]1)[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]2

Komponenten

6

Edukt 3

HCID 289CatecholHCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 521998p-Toluenesulfonic acid monohydrate

Produkt 1

HCID 67126677Ethyl spiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-4'-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of ethyl 4-oxocyclohexanecarboxylate (22.75 g) and pyrocatechol (14.75 g) in toluene (200 mL) was added catalytic amount of para-toluenesulfonic acid monohydrate and the mixture was stirred under reflux and a Dean-Stark trap overnight. The mixture was diluted with diethyl ether (600 mL) and washed with aqueous NaHCO3, water and brine. After drying over Na2SO4, the mixture was filtered and the solvent was evaporated under vacuum to provide the title compound.

Aufarbeitung

  1. temperatureunder reflux
  2. customa Dean-Stark trap overnight
  3. washwashed with aqueous NaHCO3, water and brine
  4. dry with materialAfter drying over Na2SO4
  5. filtrationthe mixture was filtered
  6. customthe solvent was evaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-78ea1e3df9a74a329e09f17a96adf1e9
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08580794B2

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