Oxalic Acid → HCID 19436559, compound

HRID 1735366Notes

Reaction equation

HRID 1735366 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[F:16][C:17]([F:29])([F:28])[O:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1.[CH2:30]([C:33]1[CH:38]=[CH:37][C:36](O)=[CH:35][CH:34]=1)[CH2:31][CH3:32].CN(C1C=CC=CN=1)C.C(O)(=O)C(O)=O>C1(C)C=CC=CC=1.O>[F:16][C:17]([F:28])([F:29])[O:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([O:25][C:36]2[CH:37]=[CH:38][C:33]([CH2:30][CH2:31][CH3:32])=[CH:34][CH:35]=2)=[O:24])=[CH:21][CH:20]=1

Participants

8

Reactant 5

HCID 971Oxalic AcidHCID 10868DicyclohexylcarbodiimideHCID 125804-PropylphenolHCID 218852-DimethylaminopyridineHCID 676134-(Trifluoromethoxy)benzoic acid

Product 1

HCID 19436559HCID 19436559, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

10.0 g of dicyclohexylcarbodiimide in 20 ml of toluene are added with water cooling to a mixture of 9.1 g of 4-trifluoromethoxybenzoic acid, 6.0 g of 4-propylphenol, 2.7 g of dimethylaminopyridine and 30 ml of toluene. The mixture is stirred for 2 hours, 1 g of oxalic acid is added, and the mixture is stirred for a further hour and filtered with suction. The filtrate is washed by shaking with 1M HCl, the phases are separated, and the organic phase is washed by shaking with 1M NaOH and worked up. After purification by chromatography and/or crystallization, 4-propylphenyl 4-(trifluoromethoxy)-benzoate having C 59° I is obtained.

Workup

  1. stirringthe mixture is stirred for a further hour
  2. filtrationfiltered with suction
  3. washThe filtrate is washed
  4. stirringby shaking with 1M HCl
  5. customthe phases are separated
  6. washthe organic phase is washed
  7. stirringby shaking with 1M NaOH
  8. customAfter purification
  9. customby chromatography and/or crystallization

Sources & evidence

ORD record
ord-aecaa45a07e34fa78dbee639c4478623
Source dataset
uspto-grants-1996_07
Patent number
US05536442

Reaction notes

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