Formic Acid → HCID 21104367, compound

HRID 1354091Notes

Reaction equation

HRID 1354091 reaction equation
[CH:1]([OH:3])=O.OO.[CH3:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[C:14]1C[CH2:17][CH2:16][CH:15]=1>O>[CH3:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[CH:14]1[CH2:15][CH2:16][CH2:17][C:1]1=[O:3]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 784Hydrogen PeroxideHCID 21104365HCID 21104365, compound

Product 1

HCID 21104367HCID 21104367, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
40 °C

Procedure

To a solution of 18 mL of 96% formic acid and 2 mL of water was added 4.5 mL of 30% hydrogen peroxide and the resulting solution was warmed to 40° C. for 10 minutes. The 1-(2,4-dimethyl-phenyl)cyclopentene (6 g) was slowly added with ice-bath cooling to maintain the internal temp at 35-40° C. The mixture was stirred at room temperature for 4 hours, diluted with water, and extracted with ether. The ether was washed with aqueous sodium bicarbonate and brine, dried, and evaporated. Purification of the residue by flash chromatography (15% ethyl acetate/hexane) afforded 2.5 g of 2-(2,4-dimethyl-phenyl)-cyclopentanone as an oil.

Workup

  1. temperaturecooling
  2. temperatureto maintain the internal temp at 35-40° C
  3. extractionextracted with ether
  4. washThe ether was washed with aqueous sodium bicarbonate and brine
  5. customdried
  6. customevaporated
  7. customPurification of the residue by flash chromatography (15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-11841423acdb46d1925c1b36064e1a75
Source dataset
uspto-grants-2007_05
Patent number
US07223767B2

Reaction notes

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