Hydrochloric Acid → (1RS,2RS)-1-hydroxy-2-methyl-5-oxo-2-phenylcyclohexane-1-carboxylic acid

HRID 324672Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 324672
[CH:1]([C:3]([CH3:5])=[O:4])=[CH2:2].[OH-].[Na+].[O:8]=[C:9]([CH:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:16])[C:10]([O:12]CC)=[O:11].Cl>C(O)C>[OH:8][C:9]1([C:10]([OH:12])=[O:11])[CH2:5][C:3](=[O:4])[CH2:1][CH2:2][C:15]1([CH3:16])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 6570Methyl vinyl ketoneHCID 14798Sodium HydroxideHCID 11435685ethyl(RS)-2-oxo-3-phenylbutyrate

Produkt 1

HCID 22004689(1RS,2RS)-1-hydroxy-2-methyl-5-oxo-2-phenylcyclohexane-1-carboxylic acidAusbeute 54,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

3.5 cm3 (39 mmol) of methyl vinyl ketone and 72 cm3 (71.5 mmol) of a normal aqueous sodium hydroxide solution were successively added to a solution, cooled to the region of 7° C., of 6.7 g (32.5 mmol) of ethyl (RS)-2-oxo-3-phenylbutyrate in 68 cm3 of ethanol and then the reaction mixture was stirred at a temperature in the region of 20° C. for two hours. The reaction mixture was cooled to 15° C. and 72 cm3 of a normal aqueous hydrochloric acid solution were added. After concentrating the ethanol, the precipitate formed was filtered off, washed with water and then dried at 50° C. 4.4 g (50%) of (1RS,2RS)-1-hydroxy-2-methyl-5-oxo-2-phenylcyclohexane-1-carboxylic acid were thus obtained in the form of a beige powder, the characteristics of which were as follows:

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to 15° C.
  2. concentrationAfter concentrating the ethanol
  3. customthe precipitate formed
  4. filtrationwas filtered off
  5. washwashed with water
  6. customdried at 50° C

Quellen und Nachweise

ORD-Eintrag
ord-3c75703ce227442fb411da74c31a54e9
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06218406B1

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