Acetone → Benzyl 3,4,5-tris(benzyloxy)benzoate

HRID 1398720Notes

Reaction equation

HRID 1398720 reaction equation
[C:1]([OH:12])(=[O:11])[C:2]1[CH:10]=[C:8]([OH:9])[C:6]([OH:7])=[C:4]([OH:5])[CH:3]=1.[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[I-].[C:22]([NH3+])([CH3:25])([CH3:24])[CH3:23].C([O-])([O-])=O.[K+].[K+].[CH3:33][C:34]([CH3:36])=O>>[CH2:13]([O:5][C:4]1[CH:3]=[C:2]([CH:10]=[C:8]([O:9][CH2:1][C:2]2[CH:10]=[CH:8][CH:6]=[CH:4][CH:3]=2)[C:6]=1[O:7][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:1]([O:12][CH2:23][C:22]1[CH:25]=[CH:36][CH:34]=[CH:33][CH:24]=1)=[O:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 5

HCID 180AcetoneHCID 370Gallic AcidHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 22344722t-Butylammonium Iodide

Product 1

HCID 45038322Benzyl 3,4,5-tris(benzyloxy)benzoateYield 80%

Procedure

A mixture of gallic acid (4 g, 21.27 mmol), benzyl chloride (19.5 mL, 0.170 mol), tertiary butyl ammonium iodide (catalytic) and K2CO3 (14.67 g, 106 mmol) in acetone (50 mL) was refluxed for 6 h. The mixture was filtered and the filter cake was washed well with acetone. The combined filtrate and washing solvent were evaporated to dryness in vacuo. The residue was dissolved in ethyl acetate (50 mL), washed with H2O (20×2 mL) and brine (30 mL), dried over Na2SO4 and evaporated to dryness. The crude residue was purified by silica gel column chromatography using 5% ethyl acetate in hexane as eluent to obtain pure 1a as white solid (9.01 g, 80%).

Workup

  1. temperaturewas refluxed for 6 h
  2. filtrationThe mixture was filtered
  3. washthe filter cake was washed well with acetone
  4. washThe combined filtrate and washing solvent
  5. customwere evaporated to dryness in vacuo
  6. dissolutionThe residue was dissolved in ethyl acetate (50 mL)
  7. washwashed with H2O (20×2 mL) and brine (30 mL)
  8. dry with materialdried over Na2SO4
  9. customevaporated to dryness
  10. customThe crude residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-18ca4c31f9a441a68a13658e94504f5e
Source dataset
uspto-grants-2014_12
Patent number
US08901317B2

Reaction notes

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