Sulfuric Acid → HCID 19862794, compound

HRID 1165261Notes

Reaction equation

HRID 1165261 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-:3])=[O:2].S(=O)(=O)(O)O.[Cl:21][CH2:22][CH2:23][CH2:24]O>C1(C)C=CC=CC=1>[Cl:21][CH2:22][CH2:23][CH2:24][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:11]([N+:13]([O-:15])=[O:14])=[CH:12][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 118802,4-Dinitrobenzoic acidHCID 123133-Chloro-1-propanol

Product 1

HCID 19862794HCID 19862794, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 106.0 g of 2,4-dinitrobenzoic acid in 200 ml of toluene were added 10.0 g of concentrated sulfuric acid and 95.0 g of 3-chloropropanol. The mixture was refluxed for 4 hrs and the resulting water removed by azeotropic distillation. After this period the mixture was cooled to room temperature and washed with 250 ml of an aqueous 5% NaHCO3 solution followed by two 200 ml water washings. The toluene was removed at reduced pressure to yield 146 g of (3-chloropropyl)-2,4-dinitrobenzoate, mp 40° C.

Workup

  1. temperatureThe mixture was refluxed for 4 hrs
  2. customthe resulting water removed by azeotropic distillation
  3. washwashed with 250 ml of an aqueous 5% NaHCO3 solution
  4. customThe toluene was removed at reduced pressure

Sources & evidence

ORD record
ord-4f2f478c798a40aabda0e0ed0daf1a2e
Source dataset
uspto-grants-1990_03
Patent number
US04908394

Reaction notes

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