Water → HCID 23146930, compound

HRID 495296Notes

Reaction equation

HRID 495296 reaction equation
[CH2:1]([C:3]1[C:8]([OH:9])=[CH:7][C:6]([OH:10])=[CH:5][C:4]=1[CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O>CC(C)=O>[CH2:22]([O:9][C:8]1[C:3]([CH2:1][CH3:2])=[C:4]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([O:10][CH2:1][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH:7]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 45093151HCID 45093151, compound

Product 1

HCID 23146930HCID 23146930, compoundYield 131.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl 2-ethyl-3,5-dihydroxyphenylacetate (1.70 g, 8.09 mmol) was dissolved in acetone (20 mL), and potassium carbonate (6.43 g, 46.5 mmol) and benzyl bromide (4.00 mL, 33.6 mmol) were added thereto ad stirred at room temperature for 6 hours. Water was added to the reaction mixture, and extracted with ethyl acetate. The organic layer was washed with aqueous saturated sodium chloride solution, then dried over anhydrous sodium sulfate, and the solvent was evaporated away under reduced pressure. The resulting residue was purified through silica gel column chromatography (n-hexane/ethyl acetate=20/1 to 9/1) to obtain methyl 3,5-bis(benzyloxy)-2-ethylphenylacetate (2.08 g, 66%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with aqueous saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated away under reduced pressure
  5. customThe resulting residue was purified through silica gel column chromatography (n-hexane/ethyl acetate=20/1 to 9/1)

Sources & evidence

ORD record
ord-56807576d68a4b50ad799b0ace753602
Source dataset
uspto-grants-2009_05
Patent number
US07538241B2

Reaction notes

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