Ammonium Chloride → HCID 67524027, compound

HRID 2241071Notes

Reaction equation

HRID 2241071 reaction equation
[CH2:1]([Mg]Cl)[CH2:2][CH2:3][CH3:4].[C:7]1(=[O:22])[C:20]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]=2[CH:10]=[CH:9][C:8]1=[O:21].[NH4+].[Cl-]>C1COCC1>[CH2:1]([C:8]1([OH:21])[C:7]([CH2:1][CH2:2][CH2:3][CH3:4])([OH:22])[C:20]2[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 30805661,2-PhenanthrenedioneHCID 178418265HCID 178418265, compound

Product 1

HCID 67524027HCID 67524027, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

300 ml of a 2.0 M solution of n-butylmagnesium chloride (0.6 mol) were added dropwise to a solution of 41.75 g (0.2 mol) of phenanthrenequinone in 800 ml of dry THF at an internal temperature of 10° C. over a period of 1.5 hours and the mixture was subsequently stirred at RT for 6 hours. After hydrolysis with 125 ml of saturated NH4Cl solution, the precipitate was filtered off with suction, washed with ethyl acetate, the filtrate was extracted twice with Water and the organic phase was dried over Na2SO4. The brown solid which remained after evaporation of the solvent was subsequently recrystallized twice from EtOH/H2O (70:30). This gave 60.6 g (93%) of colorless needles.

Workup

  1. filtrationthe precipitate was filtered off with suction
  2. washwashed with ethyl acetate
  3. extractionthe filtrate was extracted twice with Water
  4. dry with materialthe organic phase was dried over Na2SO4
  5. customafter evaporation of the solvent
  6. customwas subsequently recrystallized twice from EtOH/H2O (70:30)

Sources & evidence

ORD record
ord-480705badeea4d9ba4337a12c4c73924
Source dataset
uspto-grants-2010_05
Patent number
US07723455B2

Reaction notes

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