Trichloroisocyanuric Acid → Decanal

HRID 399609Notes

Reaction equation

HRID 399609 reaction equation
[CH2:1]([OH:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C([O-])(=O)C.[Na+].ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O>C(Cl)Cl.CC1(C)N([O])C(C)(C)CCC1>[CH:1](=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 3

HCID 6909Trichloroisocyanuric AcidHCID 81741-DecanolHCID 517045Sodium Acetate

Product 1

HCID 8175DecanalYield 98.3%

Reagents, catalysts & solvents 2

HCID 2724126TempoCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

6.08 g (38.4 mmol) of 1-decanol were dissolved in 58 ml of methylene chloride in a 200 ml sulphonation flask. 3.3 g (40.2 mmol) of sodium acetate and 3.6 g (15.5 mmol) of trichloroisocyanuric acid were added thereto. The mixture was cooled to 0° C. while stirring. A solution of 30 mg (0.12 mmol) of TEMPO derivative C in 3.5 ml of methylene chloride was dosed in within 30 minutes. The temperature was held at 0°-3° C. by constant cooling. The reaction had finished after 1 hour. The white precipitate was filtered off. The filtrate was worked up aqueous. 5.9 g (98%) of decanal were obtained as the crude product as a colourless liquid. GC content: 97% (area percent).

Workup

  1. customwas dosed in within 30 minutes
  2. customwas held at 0°-3° C. by constant cooling
  3. filtrationThe white precipitate was filtered off

Sources & evidence

ORD record
ord-53298379d49a44938508c9a5ac734917
Source dataset
uspto-grants-1998_10
Patent number
US05821374

Reaction notes

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