Sodium Hydroxide → HCID 12969134, compound

HRID 2188235Notes

Reaction equation

HRID 2188235 reaction equation
C([O:7][C:8]1[CH:9]=[C:10]([N:14]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:21][C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]2=3)[CH:11]=[CH:12][CH:13]=1)(=O)C(C)(C)C.[OH-].[Na+]>CO>[OH:7][C:8]1[CH:9]=[C:10]([N:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:27]2=3)[CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12969133HCID 12969133, compound

Product 1

HCID 12969134HCID 12969134, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 621.9 mg of N-(3′-pivaloyloxyphenyl)acridan in 20 mL of methanol containing 2.61 g of 1 M NaOH (2.6 mmol) was refluxed until TLC analysis showed the starting material had been consumed. The solvent was concentrated and the residue was dissolved in water and acidified with 1 M hydrochloric acid. The resulting precipitate was collected via suction filtration, taken up with methy.ene chloride, dried over sodium sulfate and concentrated to a crude oil. The oil was chromatographed on silica gel in 5% ethyl acetate in hexanes. The purified product was treated with hexanes and the resultant solid was collected by filtration to afford 315.8 mg of N-(3′-hydroxyphenyl)acridan (67%).

Workup

  1. customhad been consumed
  2. concentrationThe solvent was concentrated
  3. dissolutionthe residue was dissolved in water
  4. filtrationThe resulting precipitate was collected via suction filtration
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to a crude oil
  7. customThe oil was chromatographed on silica gel in 5% ethyl acetate in hexanes
  8. additionThe purified product was treated with hexanes
  9. filtrationthe resultant solid was collected by filtration

Sources & evidence

ORD record
ord-3ab6ad8d515f432893fd05f87780ffbe
Source dataset
uspto-grants-2002_06
Patent number
US06410732B2

Reaction notes

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