Formic Acid → HCID 22033997, compound

HRID 1637378Notes

Reaction equation

HRID 1637378 reaction equation
[CH2:1]([S:9][C:10]1[CH:33]=[CH:32][C:13]2=[N:14][N:15]([C:17]3[CH:22]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:20]=[C:19]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:18]=3[OH:31])[N:16]=[C:12]2[CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(O)=[O:35].OO.[OH2:39]>O.O.[O-][W]([O-])(=O)=O.[Na+].[Na+].C1(C)C(C)=CC=CC=1>[CH2:1]([S:9]([C:10]1[CH:33]=[CH:32][C:13]2=[N:14][N:15]([C:17]3[CH:22]=[C:21]([C:23]([CH3:24])([CH3:25])[CH3:26])[CH:20]=[C:19]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:18]=3[OH:31])[N:16]=[C:12]2[CH:11]=1)(=[O:35])=[O:39])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 4

HCID 284Formic AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 19349148HCID 19349148, compound

Product 1

HCID 22033997HCID 22033997, compound

Reagents, catalysts & solvents 2

HCID 150191Sodium Tungstate DihydrateCatalystHCID 7237O-XyleneSolvent2×

Conditions

Temperature
50 °C

Procedure

To a 500-mL round-bottom flask are charged 30 g (0.062 mol) of 5-n-octylthio-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole, 35 g (0.28 mol) of xylene, 6.4 g (0.12 mol) of formic acid and 0.21 g (0.0006 mol) of sodium tungstate dihydrate. The reaction mixture is heated to 50° C. and 19 g (0.28 mol) of 50% hydrogen peroxide is then added dropwise over a one-hour period such that the reaction temperature remains between 70-80° C. After holding at this temperature for two hours, 100 g of water and 100 g of xylene are added. The aqueous layer is removed and the xylene phase is washed once with 10% aqueous sodium sulfite solution, 10% aqueous potassium carbonate solution, 10% aqueous sodium chloride solution and water. Xylene is partially stripped under vacuum and 50 g of methanol are added. The yellow solution is cooled to 0-5° C. and filtered after crystallization occurs. The wetcake is washed with 100 g of cold methanol and dried to a constant weight. The title compound is obtained as yellow needles in a yield of 30.1 g (97%). The structure of the product is verified by 1HNMR and mass spectroscopy.

Workup

  1. customremains between 70-80° C
  2. customThe aqueous layer is removed
  3. washthe xylene phase is washed once with 10% aqueous sodium sulfite solution, 10% aqueous potassium carbonate solution, 10% aqueous sodium chloride solution and water
  4. additionare added
  5. temperatureThe yellow solution is cooled to 0-5° C.
  6. filtrationfiltered
  7. customafter crystallization
  8. washThe wetcake is washed with 100 g of cold methanol
  9. customdried to a constant weight

Sources & evidence

ORD record
ord-a5a9bfadbaf64876bc479fc0d2bfb6b3
Source dataset
uspto-grants-2000_03
Patent number
US06040455

Reaction notes

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