Nitric Acid → 1-(4-Methoxy-3-nitrophenyl)propan-2-one

HRID 2179889Notes

Reaction equation

HRID 2179889 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=[O:12])[CH3:11])=[CH:5][CH:4]=1.C(OC(=O)C)(=O)C.[N+:20]([O-])([OH:22])=[O:21]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=[O:12])[CH3:11])=[CH:5][C:4]=1[N+:20]([O-:22])=[O:21]

Participants

4

Reactant 3

HCID 944Nitric Acid2×HCID 7918Acetic AnhydrideHCID 312311-(p-Methoxyphenyl)-2-propanone

Product 1

HCID 224889771-(4-Methoxy-3-nitrophenyl)propan-2-oneYield 59%

Procedure

To a solution of 4-methoxyphenylacetone 9 (6.56 g, 4 mmol) in acetic anhydride (16 mmol) was added 90% HNO3 dropwise at −5° C. After adding HNO3, the ice-bath was removed and allowed to warm up to room temperature. The reaction was quenched by adding ice water. The resulting solution was extracted with ethyl acetate three times. The organic phase was dried over Na2SO4. Removal of the solvent under reduced pressure afforded crude product. Purification of the crude product by using silica gel column gave 10 (4.9 g, 59%). 1HNMR(CDCl3): 7.70 (d, J=2.1 Hz, 1H), 7.37 (dd, J=2.2 Hz, 8.5 Hz, 1H), 7.08 (d, J=8.5 Hz, 1H), 3.95 (s, 3H), 3.74 (s, 2H), 2.21 (s, 3H).

Workup

  1. customthe ice-bath was removed
  2. customThe reaction was quenched
  3. additionby adding ice water
  4. extractionThe resulting solution was extracted with ethyl acetate three times
  5. dry with materialThe organic phase was dried over Na2SO4
  6. customRemoval of the solvent under reduced pressure
  7. customafforded crude product
  8. customPurification of the crude product

Sources & evidence

ORD record
ord-a93ac836fe184adb99862141fb1f3010
Source dataset
uspto-grants-2005_05
Patent number
US06887867B2

Reaction notes

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