2-Chloro-5-nitrobenzaldehyde → 3-(5-Methyl-5-n-butoxycarbonyl-1,3-dioxolan-2-yl)-4-chloronitrobenzene

HRID 727747Notes

Reaction equation

HRID 727747 reaction equation
[OH:1][C:2]([CH3:12])([CH2:10][OH:11])[C:3]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])=[O:4].[Cl:13][C:14]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:15]=1[CH:16]=O>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:12][C:2]1([C:3]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])=[O:4])[O:1][CH:16]([C:15]2[CH:18]=[C:19]([N+:22]([O-:24])=[O:23])[CH:20]=[CH:21][C:14]=2[Cl:13])[O:11][CH2:10]1

Participants

5

Reactant 2

HCID 729332-Chloro-5-nitrobenzaldehydeHCID 14481046n-Butyl 2,3-dihydroxyisobutyrate

Product 1

HCID 144810473-(5-Methyl-5-n-butoxycarbonyl-1,3-dioxolan-2-yl)-4-chloronitrobenzeneYield 101.6%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

19.4 g of n-butyl 2,3-dihydroxyisobutyrate are added to 18.6 g of 2-chloro-5-nitrobenzaldehyde and 0.5 g of p-toluenesulfonic acid in 250 ml of toluene, and the mixture is refluxed for 5 hours under a water separator. After the mixture has been cooled, the solvent is removed and the residue is dried under greatly reduced pressure. 35 g of 3-(5-methyl-5-n-butoxycarbonyl-1,3-dioxolan-2-yl)-4-chloronitrobenzene (oil) are obtained.

Workup

  1. temperaturethe mixture is refluxed for 5 hours under a water separator
  2. temperatureAfter the mixture has been cooled
  3. customthe solvent is removed
  4. customthe residue is dried under greatly reduced pressure

Sources & evidence

ORD record
ord-031dd6ae7e694a83a1f59f9277574eb1
Source dataset
uspto-grants-1991_09
Patent number
US05045105

Reaction notes

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