Nitric Acid → HCID 11823207, compound

HRID 1781899Notes

Reaction equation

HRID 1781899 reaction equation
[N+:1]([O-:4])(O)=[O:2].[OH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:22])[CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:8][C:7]=1[O:23][CH3:24]>C(O)(=O)C.C(OCC)(=O)C>[OH:5][C:6]1[C:11]([N+:1]([O-:4])=[O:2])=[CH:10][C:9]([C:12](=[O:22])[CH2:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:8][C:7]=1[O:23][CH3:24]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 10978526HCID 10978526, compound

Product 1

HCID 11823207HCID 11823207, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.79 ml of 65 percent nitric acid in 25 ml of glacial acetic acid is added dropwise to a solution of 2.2 g of 4'-hydroxy-3'-methoxy-4- phenylbutyrophenone in 25 ml of glacial acetic acid and the mixture is stirred at room temperature for an additional 2 hours. The mixture is poured into 150 ml of ice-water and, after treatment with 20 ml of 3N hydrochloric acid, extracted three times with 75 ml of ethyl acetate each time. The organic phase is washed with water, dried over sodium sulfate and evaporated. The crude product obtained is taken up in ethyl acetate and filtered over 75 g of silica gel. After recrystallization from acetonitrile, there is obtained 4'-hydroxy-3'-methoxy-5'-nitro-4-phenylbutyrophenone in the form of yellow crystals of m.p. 120°-121°.

Workup

  1. extractionafter treatment with 20 ml of 3N hydrochloric acid, extracted three times with 75 ml of ethyl acetate each time
  2. washThe organic phase is washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe crude product obtained
  6. filtrationfiltered over 75 g of silica gel
  7. customAfter recrystallization from acetonitrile

Sources & evidence

ORD record
ord-2de9873996044fb8a14c659c901f4b0f
Source dataset
uspto-grants-1997_05
Patent number
US05633371

Reaction notes

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