Oxalic Acid → HCID 86735843, compound

HRID 866547Notes

Reaction equation

HRID 866547 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C([OH:14])(C)C.FC(F)(F)C(O)=O.C1(N=C=NC2CCCCC2)CCCCC1.C(O)(=O)C(O)=O>O.CO.CS(C)=O.C1C=CC=CC=1.N1C=CC=CC=1>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH:1]([C:10]([CH:5]([CH3:6])[CH3:4])=[O:14])([CH3:8])[CH3:2]

Participants

10

Reactant 4

HCID 971Oxalic AcidHCID 6422Trifluoroacetic acidHCID 10868DicyclohexylcarbodiimideHCID 86735844HCID 86735844, compound

Product 1

HCID 86735843HCID 86735843, compound

Reagents, catalysts & solvents 5

HCID 241BenzeneSolventHCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

Adamantane-1-isopropyl alcohol (50 gm.), 20.6 ml. pyridine, 10.3 ml. trifluoroacetic acid, 387 ml. benzene, and 387 ml. dimethylsulfoxide were added to a reaction flask and 159 gm. dicyclohexylcarbodiimide was added over 5 minutes. The mixture was stirred overnight, a solution of 70 gm. oxalic acid in 650 ml. methanol added, and the reaction mixture left 1 day at room temperature. The solution was mixed with 4 liters of water, stirred several hours, filtered and the ether separated, washed, dried and concentrated. The ether residue was taken up in a small amount of ether, filtered to remove solid, concentrated and distilled to give 37 gm. b0.025 64°-73°.

Workup

  1. waitthe reaction mixture left 1 day at room temperature
  2. stirringstirred several hours
  3. filtrationfiltered
  4. customthe ether separated
  5. washwashed
  6. customdried
  7. concentrationconcentrated
  8. filtrationfiltered
  9. customto remove solid
  10. concentrationconcentrated
  11. distillationdistilled
  12. customto give 37 gm
  13. customb0.025 64°-73°

Sources & evidence

ORD record
ord-8df26b0a3847462d8819c01b85c7a414
Source dataset
uspto-grants-1978_07
Patent number
US04100170

Reaction notes

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