p-Toluenesulfonic acid → 4-Chloro-2-(dimethoxymethyl)-1-nitrobenzene

HRID 2247887Notes

Reaction equation

HRID 2247887 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH3:13]C1C=CC(S(O)(=O)=O)=CC=1.[C:24]([O-:27])([O-])=O.[Na+].[Na+]>CC(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:7]([O:27][CH3:24])[O:8][CH3:13])[CH:9]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 10340Sodium CarbonateHCID 811235-Chloro-2-nitrobenzaldehyde

Product 1

HCID 35700934-Chloro-2-(dimethoxymethyl)-1-nitrobenzeneYield 99.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 14.7 parts of 5-chloro-2-nitrobenzaldehyde, 13.3 parts of thrimethoxymethane, 0.15 parts of 4-methylbenzenesulfonic acid and 64 parts of 2-propanol was stirred at reflux temperature until completion of the reaction. After cooling, there was added Na2CO3 and stirring was continued for 5 min. The reaction mixture was filtered and the filtrate was evaporated, yielding 18.3 parts (99.7%) of 4-chloro-2-(dimethoxymethyl)-1-nitrobenzene (interm. 8).

Workup

  1. temperatureat reflux temperature
  2. customuntil completion of the reaction
  3. temperatureAfter cooling
  4. stirringstirring
  5. filtrationThe reaction mixture was filtered
  6. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-4ddac351354646868206edfad0e01993
Source dataset
uspto-grants-1991_08
Patent number
US05037829

Reaction notes

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