Hydrochloric Acid → 6-Hydroxy-2,4,4-trimethyl-3,4-dihydro-2H-naphthalen-1-one

HRID 1870035

Reaktionsgleichung

Reaktionsgleichung von HRID 1870035
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH:8]([CH3:14])[CH2:7][C:6]2([CH3:16])[CH3:15].[C-]#N.[Na+].C#N.Cl>CS(C)=O>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH:8]([CH3:14])[CH2:7][C:6]2([CH3:15])[CH3:16]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 768Hydrogen CyanideHCID 8929Sodium CyanideHCID 211072336-methoxy-2,4,4-trimethyl-3,4-dihydro-2H-naphthalen-1-one

Produkt 1

HCID 211072316-Hydroxy-2,4,4-trimethyl-3,4-dihydro-2H-naphthalen-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A solution 6-methoxy-2,4,4-trimethyl-3,4-dihydro-2H-naphthalen-1-one (described in Journal of Pharmaceutical Sciences, 1970, 59(6), p 869-870, Floyd et al. incorporated herein by reference; 1.2 g, 5.5 mmol) and sodium cyanide (2 g, 41 mmol) in anhydrous dimethylsulfoxide (15 mL) was heated at 230° C. for 24 h under argon. The reaction mixture was then cooled to ambient temperature, poured into ice and acidified (Caution! Hydrogen cyanide evolution!) with dilute hydrochloric acid and extracted with ethyl acetate (×2). The combined organic extract was washed with brine (×1), dried over anhydrous sodium sulfate, filtered and evaporated to afford the title compound, which was used as such for the next step (1 g, 89%).

Aufarbeitung

  1. additionpoured into ice
  2. extractionextracted with ethyl acetate (×2)
  3. extractionThe combined organic extract
  4. washwas washed with brine (×1)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-16087d2915e34560b3b233118cdcaed0
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07638648B2

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