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

HRID 1968851Notes

Reaction equation

HRID 1968851 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 (80m) was refluxed until the 5-chloro-2-nitro-benzaldehyde had completely reacted. The mixture was cooled, Na2CO3 was added and stirred for 5min. The mixture was filtered off 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 off
  4. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b350ccfe790a4580b6e7f9c9e5b18063
Source dataset
uspto-grants-2013_04
Patent number
US08426429B2

Reaction notes

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