Water → 9H-xanthene-9-carbonitrile

HRID 1456677

Reaction equation

HRID 1456677 reaction equation
[C-:1]#[N:2].[K+].[CH:4]1[CH:9]=[C:8]2[CH:10](O)[C:11]3[C:16]([O:17][C:7]2=[CH:6][CH:5]=1)=[CH:15][CH:14]=[CH:13][CH:12]=3.O>C(O)(=O)C>[C:1]([CH:10]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=2[O:17][C:7]2[C:8]1=[CH:9][CH:4]=[CH:5][CH:6]=2)#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 72861Xanthydrol

Product 1

HCID 133395799H-xanthene-9-carbonitrileYield 80%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

17.5 g (0.268 mol) of potassium cyanide are added in portions to a solution, heated at 50° C., of 24.2 g (0.122 mol) of xanthydrol in 420 ml of acetic acid. The reaction mixture is subsequently stirred at 60° C. for 2 hours and then cooled, poured onto 400 ml of water and extracted with ethyl acetate/hexane=1:1. The organic phases are washed with water, combined, dried over sodium sulfate and concentrated on a vacuum rotary evaporator. Chromatography of the residue over silica gel using the mobile phase system hexane/ethyl acetate=19:1 and crystallization of the pure fractions from ether/petroleum ether gives 20.2 g (80%) of 9-cyano-xanthene, melting point 101° C. (compound (102), Table 1).

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate/hexane=1:1
  3. washThe organic phases are washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated on a vacuum rotary evaporator
  6. customChromatography of the residue over silica gel using the mobile phase system hexane/ethyl acetate=19:1 and crystallization of the pure fractions from ether/petroleum ether

Sources & evidence

ORD record
ord-f34922c06f60400ea57518d232940ae9
Source dataset
uspto-grants-1998_12
Patent number
US05844024

Linked notes

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