Acetone → ST51009822

HRID 1816409Notes

Reaction equation

HRID 1816409 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][C:14](O)=[CH:13][CH:12]=1)=[O:10].IC.[C:20](=[O:23])([O-])[O-].[K+].[K+].[CH3:26]C(C)=O>O>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:26])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:23][CH3:20])=[CH:13][CH:12]=1)=[O:10]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 11160567Methanone, (2,5-dihydroxyphenyl)(4-hydroxyphenyl)-

Product 1

HCID 4249426ST51009822Yield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (2,5-dihydroxyphenyl)(4-hydroxyphenyl)methanone (1.8 g, 7.8 mmol), iodomethane (2.3 g, 16.4 mmol), potassium carbonate (5.4 g, 39 mmol) and acetone (25 mL) was heated to reflux. After 6 h, the reaction was cooled, poured into water and extracted with EtOAc. The organic layer was dried over MgSO4, concentrated and the crude product was purified by column chromatography (eluent 10% EtOAc/hexanes) to give a yellow solid (1.2 g, 60% yield, mp 70-72° C.); 1H NMR(DMSO-d8) 11.4 (s, 1H), 7.75 (d, 2H, J=8.5 Hz), 7.15-7.11 (m, 2H), 7.03-6.98 (m, 3H), 3.90 (s, 3H), 3.73 (s, 3H); MS m/e 257 (M−H)+.

Workup

  1. temperaturewas heated to reflux
  2. temperaturethe reaction was cooled
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customthe crude product was purified by column chromatography (eluent 10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-bc7cdcb4357a4265af82498b8bf238b4
Source dataset
uspto-grants-2005_04
Patent number
US06884814B2

Reaction notes

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