Trichloroisocyanuric Acid → 4-Nitrobenzaldehyde

HRID 399610Notes

Reaction equation

HRID 399610 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].C([O-])(=O)C.[Na+].ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O>C(Cl)Cl.CC(C)=O.CC1(C)N([O])C(C)(C)CCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:8]=[O:9])=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

7

Reactant 3

HCID 6909Trichloroisocyanuric AcidHCID 692754-Nitrobenzyl alcoholHCID 517045Sodium Acetate

Product 1

HCID 5414-NitrobenzaldehydeYield 94%

Reagents, catalysts & solvents 3

HCID 2724126TempoCatalystHCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

5 g (32.6 mmol) of 4-nitrobenzylalcohol, 2.7 g (32.9 mmol) of sodium acetate and 10 mg (0.06 mmol) of TEMPO were suspended in 40 ml of methylene chloride in a 100 ml sulphonation flask and the suspension was cooled to (-8)-(-10)° C. while stirring. A solution of 3.03 g (13.0 mmol) of trichloroisocyanuric acid in 20 ml of acetone was dosed in within 1 hour, whereupon the mixture was held at (-5)° C. for 1 hour. Thereafter, the reaction had finished. The white precipitate was filtered off and the filtrate was washed with sodium bicarbonate solution and with sodium chloride solution. The organic phase was concentrated and the residue was recrystallized from diisopropyl ether. There were obtained 4.62 g (94%) of 4-nitrobenzaldehyde, GC content: (97.7%) (area percent).

Workup

  1. temperaturethe suspension was cooled to (-8)-(-10)° C
  2. customwas dosed in within 1 hour, whereupon the mixture
  3. filtrationThe white precipitate was filtered off
  4. washthe filtrate was washed with sodium bicarbonate solution and with sodium chloride solution
  5. concentrationThe organic phase was concentrated
  6. customthe residue was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-8f22759a0748474c8c8827a6df383c7f
Source dataset
uspto-grants-1998_10
Patent number
US05821374

Reaction notes

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