Acetic Acid → HCID 23134154, compound

HRID 2220621Notes

Reaction equation

HRID 2220621 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([CH3:22])[C:12]=1[B:13]1[O:17]C(C)(C)C(C)(C)[O:14]1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].C(O)(=O)C.O.O1CCOCC1>C(OCC)(=O)C>[CH2:8]([O:7][C:5]([C:4]1[CH:10]=[C:11]([CH3:22])[C:12]([B:13]([OH:17])[OH:14])=[C:2]([CH3:1])[CH:3]=1)=[O:6])[CH3:9]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962Water2×HCID 312751,4-DioxaneHCID 23134218HCID 23134218, compound

Product 1

HCID 23134154HCID 23134154, compoundYield 27.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of ethyl 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (0.233 g), acetic acid (0.2 mL), water (2 mL) and 1,4-dioxane (2 mL) was stirred at 75° C. for 2 days. Water and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/5-1/3) to afford 4-ethoxycarbonyl-2,6-dimethylphenylboronic acid (0.047 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/5-1/3)

Sources & evidence

ORD record
ord-49c76bcbf3244cdaa6c89a7a20fda86a
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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