Potassium Hydroxide → HCID 22145692, compound

HRID 1983579Notes

Reaction equation

HRID 1983579 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([O:9][CH:10]([CH3:12])[CH3:11])[C:6]([O:13][CH3:14])=[CH:5][N:4]=1.[Mn]([O-])(=O)(=O)=[O:16].[K+].[OH-].[K+]>O.C(O)(C)C>[CH:10]([O:9][C:7]1[C:6]([O:13][CH3:14])=[CH:5][N:4]=[C:3]([C:2]([OH:16])=[O:1])[CH:8]=1)([CH3:11])[CH3:12]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 516875Potassium PermanganateHCID 68845071HCID 68845071, compound

Product 1

HCID 22145692HCID 22145692, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolCatalystHCID 962WaterSolvent2×

Conditions

Temperature
70 °C

Procedure

To a stirred and heated (50° C.) solution of the product of step 1 (0.410 g, 2.08 mmol) in water (12 mL) was added, portionwise over 30 minutes, solid potassium permanganate (0.680 g, 4.30 mmol). Following the addition, reaction temperature was increased to 70° C. After 45 minutes the reaction was cooled to room temperature and treated with a solution of potassium hydroxide (0.230 g, 4.10 mmol) in water (6 mL) followed by a few drops of isopropanol. The mixture was stirred for about 5 minutes before filtering through Celite. The filtrate was concentrated to dryness under a nitrogen current. The resulting brown residue was dissolved in water (10 mL), adjusted to pH 2 with concentrated hydrochloric acid and extracted repeatedly with chloroform. The combined extracts were dried (sodium sulfate) and concentrated to afford 0.414 g (94%) of product as a pink-gray foam: 1H NMR (DMSO-d6) δ 8.23 (s, 1H), 7.5 8 (s, 1H), 4.81 (sept, J=6.0 Hz, 1H), 3.90 (s, 3H), 1.29 (d, J=6.0 Hz, 6H) ppm.

Workup

  1. additionwas added, portionwise over 30 minutes
  2. additionthe addition, reaction temperature
  3. temperatureAfter 45 minutes the reaction was cooled to room temperature
  4. stirringThe mixture was stirred for about 5 minutes
  5. filtrationbefore filtering through Celite
  6. concentrationThe filtrate was concentrated to dryness under a nitrogen current
  7. dissolutionThe resulting brown residue was dissolved in water (10 mL)
  8. extractionextracted repeatedly with chloroform
  9. dry with materialThe combined extracts were dried (sodium sulfate)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-9549fbe8eaa044ceb6eb1694d73b97c6
Source dataset
uspto-grants-2009_06
Patent number
US07541466B2

Reaction notes

Loading…