Acetic Acid → HCID 178515946, compound

HRID 498917Notes

Reaction equation

HRID 498917 reaction equation
[CH:1]1[CH:20]=[CH:19][C:17](=[O:18])/[C:3](=[CH:4]/[NH:5][CH2:6][CH2:7][NH:8]/[CH:9]=[C:10]2/[CH:11]=[CH:12][CH:13]=[CH:14][C:15]/2=[O:16])/[CH:2]=1.O.O.O.O.C([O-])(=O)C.[Co+2:29].C([O-])(=O)C.C(O)(=O)C.[N+](C1C=C(C=C([N+]([O-])=O)C=1)C(O)=O)([O-])=O>C(Cl)Cl.C1(C)C=CC=CC=1>[Co+3:29].[CH:12]1[CH:13]=[CH:14][C:15](=[O:16])/[C:10](=[CH:9]/[NH:8][CH2:7][CH2:6][NH:5]/[CH:4]=[C:3]2/[CH:2]=[CH:1][CH:20]=[CH:19][C:17]/2=[O:18])/[CH:11]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 74333,5-Dinitrobenzoic acidHCID 61372Cobalt(II) acetate tetrahydrateHCID 178515945HCID 178515945, compound

Product 1

HCID 178515946HCID 178515946, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of ‘salen’ ligand (7e) (43 mg, 0.045 mmol, 1 equiv.) in 5 mL CH2Cl2, a methanolic (2 mL) solution of cobalt (II) acetate tetrahydrate (11.4 mg, 45 μmol, 1.0 equiv.), was added via cannula, under Ar. The Co(II)-salen complex precipitated out as a red solid. After filtration, the Co(II) complex was taken up in CH2Cl2 or toluene (2 mL) and stirred with acetic acid (>10 equiv.) or 3,5-dinitrobenzoic acid (1 equiv.) open to the air. The oxidation was followed by TLC, formation of a greenish-brown spot of lower Rf {Co-(III) complex} from the visibly red, higher Rf spot characteristic of the Co-(II) salen. When TLC indicated the completion of the reaction (2-12 h), the solvent was evaporated, and the Co(III)-salen complex further dried in vacuo. The Co(III) carboxylate complexes so prepared were used for HKR experiments, under ISES (bilayer) conditions or under neat ‘Jacobsen’ (conventional) conditions.

Workup

  1. customThe Co(II)-salen complex precipitated out as a red solid
  2. filtrationAfter filtration
  3. customthe completion of the reaction (2-12 h)
  4. customthe solvent was evaporated
  5. customthe Co(III)-salen complex further dried in vacuo
  6. customThe Co(III) carboxylate complexes so prepared

Sources & evidence

ORD record
ord-c0f0d65070b249b1836a1d83c27ed736
Source dataset
uspto-grants-2010_08
Patent number
US07767388B2

Reaction notes

Loading…