Nitric Acid → 1-(2-Methyl-5-nitrophenyl)ethan-1-one

HRID 848657Notes

Reaction equation

HRID 848657 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].[N+:11]([O-])([OH:13])=[O:12]>S(=O)(=O)(O)O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:11]([O-:13])=[O:12])=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 113402-Methylacetophenone

Product 1

HCID 205638251-(2-Methyl-5-nitrophenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To 120 ml of concentrated sulfuric acid is added 53.6 g of o-methylacetophenone, while cooling at -10°. To this cold, stirred solution is added a mixture of 32 ml of 70% nitric acid and 48 ml of concentrated sulfuric acid. The reaction solution is stirred for 21/2 hours between -9° and 0° and then poured over 800 g of ice. The mixture is extracted with ether and the organic phase washed with water, saturated Na2CO3 solutions, water and finally brine. The ether solution is dried over MgSO4 and evaporated to dryness to give 56.2 g of a pale yellow oil. The oil is crystallized from 95% ethanol to give 25.4 g of product, mp about 50° C. Recrystallization from hexane afforded product mp 53°-55° C.

Workup

  1. temperaturewhile cooling at -10°
  2. additionis added
  3. stirringThe reaction solution is stirred for 21/2 hours between -9° and 0°
  4. extractionThe mixture is extracted with ether
  5. washthe organic phase washed with water, saturated Na2CO3 solutions, water and finally brine
  6. dry with materialThe ether solution is dried over MgSO4
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-2a3fabf976654d99bffe4c8c39b9b879
Source dataset
uspto-grants-1981_10
Patent number
US04297127

Reaction notes

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