Acetic Acid → HCID 86620126, compound

HRID 1664835Notes

Reaction equation

HRID 1664835 reaction equation
[Mn]([O-])(=O)(=O)=O.[K+].[CH3:7][C:8]([CH3:26])=[CH:9][CH2:10][N:11]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].C(O)(=[O:29])C.[OH2:31]>CC(C)=O>[OH:31][C:8]([CH3:26])([CH3:7])[C:9](=[O:29])[CH2:10][N:11]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 516875Potassium PermanganateHCID 9994105HCID 9994105, compound

Product 1

HCID 86620126HCID 86620126, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium permanganate (114 mg, 0.72 mmol) was added to a solution of di-tert-butyl (3-methylbut-2-en-1-yl)imidodicarbonate (115 mg, 0.40 mmol) in acetone (0.8 mL), water (0.2 mL), and glacial acetic acid (20 μL). After 4 h, the reaction was quenched with saturated aqueous sodium sulfite. The mixture was adjusted to pH 5 with aqueous hydrochloric acid and extracted with ethyl acetate (3×). The combined organic extracts were washed with saturated aqueous sodium bicarbonate, saturated brine, dried over magnesium sulfate, filtered and concentrated. MS 340.1 (M+Na).

Workup

  1. customthe reaction was quenched with saturated aqueous sodium sulfite
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined organic extracts were washed with saturated aqueous sodium bicarbonate, saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-30e3829dd5f14b049ff218c78922d3fe
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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