Potassium Iodide → Methyl 3,4,5-Tris(benzyloxy)benzoate

HRID 1894916Notes

Reaction equation

HRID 1894916 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:13])[C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].[CH2:14](Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[CH2:14]([O:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:13][CH2:5][C:4]2[CH:9]=[CH:10][CH:11]=[CH:2][CH:3]=2)[C:11]=1[O:12][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:5]([O:7][CH3:8])=[O:6])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7428Methyl GallateHCID 7503Benzyl ChlorideHCID 11430Potassium Carbonate

Product 1

HCID 352181Methyl 3,4,5-Tris(benzyloxy)benzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl 3,4,5-trihydroxybenzoate (16) (55.24 g, 0.3 mol), benzyl chloride (113.93 g, 0.9 mol), dry potassium carbonate (124.39 g, 0.9 mol) and potassium iodide (catalytic amount) were stirred in refluxing dry acetone (600 mL) for 12 h. After cooling, the acetone was evaporated, and the solution was dissolved in water (250 mL). The water phase was extracted with diethyl ether (4×100 mL), the organic phase was washed with brine (2×50 mL), dried (MgSO4) and the solvent was removed in vacuo. Recrystallisation from petroleum ether and ethyl acetate gave the titled compound as white crystals, m.p. 102-103° C. Yield: 121.4 g (89%). Spectroscopic data were in accordance with the literature (J. Barbera, R. Iglesias, J. L. Serrano, T. Sierra, M. R. de la Fuente, B. Palacios, M. A. Perez-Jubindo, J. T. Vazquez, J. Am. Chem. Soc. 1998, 120, 2908).

Workup

  1. temperatureAfter cooling
  2. customthe acetone was evaporated
  3. dissolutionthe solution was dissolved in water (250 mL)
  4. extractionThe water phase was extracted with diethyl ether (4×100 mL)
  5. washthe organic phase was washed with brine (2×50 mL)
  6. dry with materialdried (MgSO4)
  7. customthe solvent was removed in vacuo
  8. customRecrystallisation from petroleum ether and ethyl acetate

Sources & evidence

ORD record
ord-572d3b48ce6348118f19fbc89d392945
Source dataset
uspto-grants-2013_08
Patent number
US08513395B2

Reaction notes

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