Acetone → HCID 58481591, compound

HRID 509166Notes

Reaction equation

HRID 509166 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH:9]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)O)=[C:4]([CH3:16])[CH:3]=1.CC(C)=[O:19].P(=O)(O)(O)O>O>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH:9]2[C:13](=[O:12])[CH:14]=[CH:15][CH:11]2[OH:19])=[C:4]([CH3:16])[CH:3]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 1004Phosphoric AcidHCID 67109386HCID 67109386, compound

Product 1

HCID 58481591HCID 58481591, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of (4-fluoro-2,6-dimethylphenyl)furan-2-ylmethanol (6 g, 27 mmol), acetone (150 ml), water (24 ml) and orthophosphoric acid (0.6 ml) is heated under microwave conditions at 120° C. for 50 minutes. The organic solvent is evaporated under vacuo, diluted with water (150 ml) and extracted with ethylacetate (3×100 ml). The combined organic extracts are combined, washed with water and brine, dried over anhydrous sodium sulphate, filtered and the filtrate is concentrated in vacuo. The residue is purified by column chromatography on silica gel to give 5-(4-fluoro-2,6-dimethylphenyl)-4-hydroxy cyclopent-2-enone (3 g).

Workup

  1. customThe organic solvent is evaporated under vacuo
  2. additiondiluted with water (150 ml)
  3. extractionextracted with ethylacetate (3×100 ml)
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated in vacuo
  8. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f5d5fd695f1d43cc96b03e24b128e625
Source dataset
uspto-grants-2015_08
Patent number
US09096560B2

Reaction notes

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