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

HRID 463498Notes

Reaction equation

HRID 463498 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-63f8578bf75941b59229577461996298
Source dataset
uspto-grants-1985_05
Patent number
US04519938

Reaction notes

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