Sodium Hydroxide → 1-(4-Amino-3-benzoylphenyl)ethan-1-one

HRID 1380009Notes

Reaction equation

HRID 1380009 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([C:16]2([CH3:21])OCC[O:17]2)=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].Cl(O)(=O)(=O)=O.[OH-].[Na+]>C(O)C>[C:16]([C:13]1[CH:14]=[CH:15][C:2]([NH2:1])=[C:3]([CH:12]=1)[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:5])(=[O:17])[CH3:21]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24247Perchloric AcidHCID 21828105[2-Amino-5-(2-methyl-1,3-dioxolan-2-yl)phenyl](phenyl)methanone

Product 1

HCID 132971931-(4-Amino-3-benzoylphenyl)ethan-1-oneYield 93.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Amino-5-(2-methyl-1,3-dioxolan-2-yl)benzophenone (1.0 g, 3.54 m mol) was dissolved in 30 ml absolute ethanol. To this was added 1M perchloric acid (14 ml). The resulting mixture was stirred at room temperature for 18 hrs. The mixture was made basic with 3N sodium hydroxide solution and then extracted with several portions of methylene chloride. The combined methylene chloride extracts were washed with water, dried with anhydrous sodium sulfate, and evaporated to yield a yellow product (0.79 g) of mp. 158°-161° C. A portion of the product was recrystallized from a mixture of methylene chloride and hexane to yield material of mp. 158°-162° C.

Workup

  1. extractionextracted with several portions of methylene chloride
  2. washThe combined methylene chloride extracts were washed with water
  3. dry with materialdried with anhydrous sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-2d91091396e343bdb3fc7fa4afa1f9e4
Source dataset
uspto-grants-1986_04
Patent number
US04579679

Reaction notes

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