Toluene → 5-Chloro-2-nitrobenzaldehyde diethyacetal

HRID 1681383Notes

Reaction equation

HRID 1681383 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].[C:13]1([CH3:19])C=CC=CC=1.[OH2:20].[C:21]1(C)C=CC(S(O)(=O)=O)=C[CH:22]=1>O>[CH2:21]([O:8][CH:7]([O:20][CH2:13][CH3:19])[C:6]1[CH:9]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[N+:10]([O-:12])=[O:11])[CH3:22]

Participants

5

Reactant 3

HCID 1140TolueneHCID 811235-Chloro-2-nitrobenzaldehydeHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 132362995-Chloro-2-nitrobenzaldehyde diethyacetalYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-chloro-2-nitrobenzaldehyde (5.0 g), toluene (50 ml), p-toluenesulfonic acid monohydrate (25 mg) was heated under stirring for 2 hours by dehydrating water which was formed in the course of reaction. The solvent was distilled under reduced pressure and the residue was column chromatographed (hexane/ethyl acetate: 8/1) to give 6.5 g of the pure title compound (93%).

Workup

  1. temperaturewas heated
  2. customwas formed in the course of reaction
  3. distillationThe solvent was distilled under reduced pressure
  4. customchromatographed (hexane/ethyl acetate: 8/1)

Sources & evidence

ORD record
ord-762d8d9f3b824d3d867bce3db879c174
Source dataset
uspto-grants-1992_12
Patent number
US05171851

Reaction notes

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