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

HRID 2088809Notes

Reaction equation

HRID 2088809 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)C=O.[CH3:13][O:14][CH:15](OC)[O:16][CH3:17].CC1C=CC(S(O)(=O)=O)=CC=1.C([O-])([O-])=O.[Na+].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:15]([O:16][CH3:17])[O:14][CH3:13])[CH:9]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 10340Sodium CarbonateHCID 811235-Chloro-2-nitrobenzaldehyde2×

Product 1

HCID 35700934-Chloro-2-(dimethoxymethyl)-1-nitrobenzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-chloro-2-nitro-benzaldehyde (0.0792 mol), trimethoxy-methane (0.126 mol) and PTSA (0.00079 mol) in methanol (80 mL) was refluxed until the 5-chloro-2-nitro-benzaldehyde had completely reacted. The mixture was cooled, Na2CO3 was added, and the reaction mixture was stirred for 5 min. The mixture was filtered and the filtrate was evaporated under reduced pressure to yield the title compound as a residue.

Workup

  1. customhad completely reacted
  2. temperatureThe mixture was cooled
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1933d30a0f0d45a487af47a3ab9a9419
Source dataset
uspto-grants-2013_05
Patent number
US08436006B2

Reaction notes

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