4-Nitrobenzaldehyde → 1-(dimethoxymethyl)-4-nitrobenzene

HRID 876117Notes

Reaction equation

HRID 876117 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7](C=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[CH3:29][O:30][CH:31](OC)[O:32][CH3:33]>CO>[CH3:29][O:30][CH:31]([O:32][CH3:33])[C:7]1[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 5414-NitrobenzaldehydeHCID 9005Trimethyl orthoformateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 5971651-(dimethoxymethyl)-4-nitrobenzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A flask equipped with a magnetic stir bar and vigreux column was charged with 4-nitro-benzaldehyde (5.0 g, 33.1 mmol), pyridinium p-toluenesulfonate (1.66 g, 6.62 mmol), trimethoxymethane (3.51 g, 33.1 mmol) and methanol (100 mL). The mixture was heated at 50° C. for 12 h and was concentrated in vacuo. The residue was redissolved in EtOAc and washed with aq. NaOH (1M), H2O and brine. The mixture was dried (Na2SO4), filtered and concentrated in vacuo to yield the title compound as a clear, light yellow oily product (6.36 g, 97%).

Workup

  1. customA flask equipped with a magnetic stir bar
  2. concentrationwas concentrated in vacuo
  3. dissolutionThe residue was redissolved in EtOAc
  4. washwashed with aq. NaOH (1M), H2O and brine
  5. dry with materialThe mixture was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-428d78772c16457c90d89936d17168e3
Source dataset
uspto-grants-2015_03
Patent number
US08986740B2

Reaction notes

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