Oxalic Acid → HCID 57173889, compound

HRID 2249077Notes

Reaction equation

HRID 2249077 reaction equation
O[CH:2]([CH2:7][CH2:8][S:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:22])([F:21])[CH:18]([F:20])[F:19])=[CH:12][CH:11]=1)[CH2:3][C:4](=[O:6])[CH3:5].C(O)(=O)C(O)=O>C1(C)C=CC=CC=1>[F:22][C:17]([F:21])([O:16][C:13]1[CH:14]=[CH:15][C:10]([S:9][CH2:8][CH2:7][CH:2]=[CH:3][C:4](=[O:6])[CH3:5])=[CH:11][CH:12]=1)[CH:18]([F:20])[F:19]

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 14534473HCID 14534473, compound

Product 1

HCID 57173889HCID 57173889, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

12.48 Grams of 4-hydroxy-6-[4-(1,1,2,2-tetrafluoroethoxy)phenylthio]-2-hexanone were dissolved in 150 ml of toluene, and 1.50 g of oxalic acid were added thereto. The resulting mixture was refluxed for 2 hours with stirring, allowed to cool and then treated in the same manner as in Production example 34. Thus, 11.76 g of 6-[4-(1,1,2,2-tetrafluoroethoxy)phenylthio]-3-hexen-2-one (trans : cis =4.6 : 1) were obtained (purity: 98.0%). Further, the product was column chromatographed to obtain a purified product having a refractive index (nD23) of 1.5202. The yield was 96.8%.

Workup

  1. temperatureThe resulting mixture was refluxed for 2 hours
  2. temperatureto cool
  3. additiontreated in the same manner as in Production example 34

Sources & evidence

ORD record
ord-2f577c1cfa944d1db6c3fe19275113f8
Source dataset
uspto-grants-1991_08
Patent number
US05041679

Reaction notes

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