Butyryl chloride → 2-Butyryl-5,5-dimethyl-3-hydroxy-4-phenylcyclohex-2-ene-1-one

HRID 1031322Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1031322
[CH3:1][C:2]1([CH3:16])[CH2:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])[CH:3]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH3:17][CH2:18][CH2:19][C:20](Cl)=[O:21].C(OC1CC(C)(C)C(C2C=CC=CC=2)C(=O)C=1)(=O)CCC.C(OC1C(C2C=CC=CC=2)C(C)(C)CC(=O)C=1)(=O)CCC>C(Cl)Cl.C1(C)C=CC=CC=1.C(N(CC)CC)C>[C:20]([C:5]1[C:6](=[O:8])[CH2:7][C:2]([CH3:16])([CH3:1])[CH:3]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:4]=1[OH:9])(=[O:21])[CH2:19][CH2:18][CH3:17]

Komponenten

8

Edukt 4

HCID 8855Butyryl chlorideHCID 130878735,5-Dimethyl-4-phenylcyclohexane-1,3-dioneHCID 221675371-Butyryloxy-5,5-di-methyl-4-phenyl cyclohex-1-ene-3-oneHCID 22167538HCID 22167538, Verbindung

Produkt 1

HCID 221675352-Butyryl-5,5-dimethyl-3-hydroxy-4-phenylcyclohex-2-ene-1-oneAusbeute 42,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Triethylamine (5.2 g) was added dropwise to a stirred solution of 5,5-dimethyl-4-phenyl cyclohexane-1,3-dione (10.8 g) and n-butyryl chloride (5.3 g) in methylene chloride (100 ml). After stirring at ambient temperature for a further 2 hours, the reaction solution was washed with water and brine and dried over anhydrous magnesium sulphate. The methylene chloride was removed in vacuo to give a mixture of 1-butyryloxy-5,5-di-methyl-4-phenyl cyclohex-1-ene-3-one and 1-butyryloxy-5,5-dimethyl-6-phenyl cyclohex-1-ene-3-one. Toluene (100 ml) was added, followed by 4-(N-dimethylamino) pyridine (1 g) and the mixture was refluxed for 3 hours. Evaporation of the toluene in vacuo gave a red oil which was purified on a silica gel column using 5% (v/v) diethyl ethermethylene chloride as eluant to give the title compound (6 g) as a pale yellow oil.

Aufarbeitung

  1. washthe reaction solution was washed with water and brine
  2. dry with materialdried over anhydrous magnesium sulphate
  3. customThe methylene chloride was removed in vacuo
  4. customto give
  5. temperaturethe mixture was refluxed for 3 hours
  6. customEvaporation of the toluene in vacuo
  7. customgave a red oil which
  8. customwas purified on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-cbfe722454414d08a98a0df6b5acecdb
Quelldatensatz
uspto-grants-1990_09
Patentnummer
US04954160

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