Methanol → 1-(1,1-Dimethoxyethyl)-4-nitrobenzene

HRID 2361517Notes

Reaction equation

HRID 2361517 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:13][O:14]C(OC)OC.[CH3:20]O>CC1C=CC(S(O)(=O)=O)=CC=1.C([O-])([O-])=O.[Na+].[Na+]>[CH3:20][O:12][C:10]([C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)([O:14][CH3:13])[CH3:11]

Participants

6

Reactant 3

HCID 887MethanolHCID 7487p-NitroacetophenoneHCID 9005Trimethyl orthoformate

Product 1

HCID 124033621-(1,1-Dimethoxyethyl)-4-nitrobenzeneYield 100%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 10340Sodium CarbonateCatalyst

Procedure

To a solution of 1-(4-nitrophenyl)ethanone (5 g, 30 mmol) in MeOH was added trimethoxymethane (3.2 g, 30 mmol) followed by 4-methylbenzenesulfonic acid (29 mg, 0.15 mmol). The mixture was stirred for 72 h and quenched by adding solid Na2CO3 (16 mg, 0.15 mmol). Stirring was continued for 30 min and the mixture was filtered through a neutral alumina pad. The filtrate was concentrated and the crude product was re-crystallized with MeOH to afford the title compound as a white solid (6.4 g, 100%). MS (ESI) m/z [M+H]+212.

Workup

  1. customquenched
  2. stirringStirring
  3. waitwas continued for 30 min
  4. filtrationthe mixture was filtered through a neutral alumina pad
  5. concentrationThe filtrate was concentrated
  6. customthe crude product was re-crystallized with MeOH

Sources & evidence

ORD record
ord-aae43c4cc8c9467fae47bfb9ec5f04dd
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

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