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

HRID 2249196Notes

Reaction equation

HRID 2249196 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-nitrobenzaldehyde

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 14.7 parts of 5-chloro-2-nitrobenzaldehyde, 13.3 parts of trimethoxymethane, 0.15 parts of 4-methylbenzenesulfonic acid and 64 parts of methanol was stirred at reflux temperature. After cooling, the reaction mixture was neutralized with sodium carbonate and stirred for 5 min. The whole was filtered and the filtrate was evaporated, yielding 18.3 parts (99.7%) of 4-chloro-2-(dimethoxymethyl)-1-nitrobenzene (interm. 43).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. stirringstirred for 5 min
  4. filtrationThe whole was filtered
  5. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-89164227774443879569daa4b56a00d8
Source dataset
uspto-grants-1991_08
Patent number
US05043327

Reaction notes

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