Nitric Acid → 1-(4-(Benzyloxy)-5-methoxy-2-nitrophenyl)ethanone

HRID 2277400Notes

Reaction equation

HRID 2277400 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][C:10]=1[O:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:20]([O-])([OH:22])=[O:21].S(=O)(=O)(O)O>C(Cl)Cl>[CH2:1]([O:8][C:9]1[C:10]([O:18][CH3:19])=[CH:11][C:12]([C:15](=[O:17])[CH3:16])=[C:13]([N+:20]([O-:22])=[O:21])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 944Nitric Acid2×HCID 1118Sulfuric AcidHCID 992151-(4-Benzyloxy-3-methoxy-phenyl)-ethanone

Product 1

HCID 534867601-(4-(Benzyloxy)-5-methoxy-2-nitrophenyl)ethanoneYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-benzyloxy-3-methoxyphenyl)ethanone (51.3 g, 200 mmol) in DCM (750 mL) at 0° C. was added nitric acid (68%, 21 mL, 300 mmol) dropwise over 20 minutes, followed by sulfuric acid (98%, 16.3 mL, 300 mmol) over 40 minutes. Additional nitric acid (14.3 mL, 200 mmol) was added dropwise for another 20 minutes. The reaction mixture was then washed with water until the pH was 7˜8, dried over Na2SO4, and concentrated in vacuo. The residue was recrystallized from ethanol (850 mL) to give the title compound as a light yellow solid (40 g, 68%).

Workup

  1. washThe reaction mixture was then washed with water until the pH was 7˜8
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was recrystallized from ethanol (850 mL)

Sources & evidence

ORD record
ord-8888128a5f0246ba83558a66ce69fb3c
Source dataset
uspto-grants-2015_09
Patent number
US09133162B2

Reaction notes

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