Oxalic Acid → HCID 57257765, compound

HRID 2249100Notes

Reaction equation

HRID 2249100 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][CH:11](O)[CH2:12][C:13](=[O:15])[CH3:14])=[CH:4][CH:3]=1.C(O)(=O)C(O)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][CH2:9][CH2:10][CH:11]=[CH:12][C:13](=[O:15])[CH3:14])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 14883916HCID 14883916, compound

Product 1

HCID 57257765HCID 57257765, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

15.51 Grams of 6-(4-chlorophenylthio)-4-hydroxy-2-hexanone was dissolved in 100 ml of toluene, and 0.92 g of oxalic acid was added thereto. The resulting mixture was refluxed for 4 hours with stirring. After having been cooled, the mixture was washed with a saturated aqueous sodium hydrogencarbonate solution and then saturated aqueous sodium chloride solution. Then the mixture was dried over anhydrous magnesium sulfate. Removing the solvent from the mixture under reduced pressure gave 14.22 g of 6-(4-chlorophenyl-thio)-3-hexen-2-one. (trans : cis =3.1 : 1) (purity: 98.0%). The yield was 96.6%. A purified product was obtained by column chromatography. The purified product had an nD24 of 1.5953.

Workup

  1. temperatureThe resulting mixture was refluxed for 4 hours
  2. temperatureAfter having been cooled
  3. washthe mixture was washed with a saturated aqueous sodium hydrogencarbonate solution
  4. dry with materialThen the mixture was dried over anhydrous magnesium sulfate
  5. customRemoving the solvent from the mixture under reduced pressure

Sources & evidence

ORD record
ord-7758c02f093544fda9e06ba6a1648d87
Source dataset
uspto-grants-1991_08
Patent number
US05041679

Reaction notes

Loading…