4-Isopropylphenol → 3-(4-Isopropyl-phenoxy)-pentane-2,4-dione

HRID 1410379Notes

Reaction equation

HRID 1410379 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[N+](=[C:13]([C:17](=[O:19])[CH3:18])[C:14](=[O:16])[CH3:15])=[N-]>C1C=CC=CC=1.C([O-])(=O)C.[Rh+2].C([O-])(=O)C>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH:13]([C:17](=[O:19])[CH3:18])[C:14](=[O:16])[CH3:15])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 74654-IsopropylphenolHCID 5369133-diazo-pentane-2,4-dione

Product 1

HCID 221748743-(4-Isopropyl-phenoxy)-pentane-2,4-dioneYield 39.4%

Reagents, catalysts & solvents 2

HCID 21674Acetic acid, rhodium(2+) saltCatalystHCID 241BenzeneSolvent2×

Procedure

To a refluxing solution of 4-isopropylphenol (0.548 g, 4.02 mmol) and rhodium(II) acetate (ca. 15 mgs) in benzene (10 mL) was added a solution of 3-diazo-pentane-2,4-dione (0.507 g, 4.02 mmol) in benzene (20 mL) over 40 minutes. The reaction mixture was allowed to cool to room temperature and was concentrated to afford a green oil. Flash chromatography over silica (ethyl acetate/hexanes) provided 0.371 g (39%) of the product as a white solid: 1H NMR (CDCl3) δ 14.4 (s, 1H), 7.15 (d, J=8.6 Hz, 2H), 6.82 (d, J=8.6 Hz, 2H), 2.87 (sept, J=7.0 Hz, 1H), 2.04, (s, 6H), 1.23 (d, J=7.0 Hz, 6H) ppm.

Workup

  1. concentrationwas concentrated
  2. customto afford a green oil

Sources & evidence

ORD record
ord-5bb8fdb862714b338c6769737647d45f
Source dataset
uspto-grants-2014_12
Patent number
US08921547B2

Reaction notes

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