Ethanol → HCID 68688462, compound

HRID 2244209Notes

Reaction equation

HRID 2244209 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[CH:5]=1.[CH2:12](O)[CH3:13].O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.CCCCCC.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]([C:3]2[C:4]([CH3:9])=[CH:5][CH:6]=[CH:7][C:12]=2[CH3:13])=[C:6]([CH3:10])[CH:5]=1)=[O:11]

Participants

8

Reactant 4

HCID 702EthanolHCID 962WaterHCID 7435Benzoic acid, 3-methyl-, methyl esterHCID 10340Sodium Carbonate

Product 1

HCID 68688462HCID 68688462, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2,6-Dimethyl boronic acid (13.7 g, 91 mmol) and 3-methyl benzoic acid methyl ester (20.9 g, 91 mmol) were dissolved in toluene (425 mL). Then ethanol (250 mL) and water (250 mL) were added followed by sodium carbonate (38.7 g, 365 mmol). The system was purged with nitrogen and then tetrakis triphenylphospine palladium(0) catalyst (10.5 g, 9 mmol) was added. The mixture was heated under nitrogen for 21 hours and filtered through celite. The cake was washed with a large amount of ethyl acetate, the combined filtrate was washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated to give a solid. Flash chromatography of the residue over silica gel Merck-60 using a gradient of 0-20% ethyl acetate in hexane as the eluant, gave the title compound as a white solid (19.2 g, 83%).

Workup

  1. customThe system was purged with nitrogen
  2. temperatureThe mixture was heated under nitrogen for 21 hours
  3. filtrationfiltered through celite
  4. washThe cake was washed with a large amount of ethyl acetate
  5. washthe combined filtrate was washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customto give a solid

Sources & evidence

ORD record
ord-f83eff37a5594451a605b2d08ce691e1
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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