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

HRID 1760892Notes

Reaction equation

HRID 1760892 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][O:10][C:11](=[O:21])[C:12]1[CH:17]=[C:16]([OH:18])[C:15]([OH:19])=[C:14]([OH:20])[CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CC(C)=O.O>[CH3:9][O:10][C:11](=[O:21])[C:12]1[CH:13]=[C:14]([O:20][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:15]([O:19][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:16]([O:18][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:17]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 7428Methyl GallateHCID 7503Benzyl ChlorideHCID 10340Sodium Carbonate

Product 1

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

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

105 g (0.83 mol) of benzyl chloride are added dropwise at 56° C., under reflux, over a period of 10 minutes, to 18.4 g (0.1 mol) of 3,4,5-trihydroxybenzoic acid methyl ester, 50.0 g (0.48 mol) of sodium carbonate and 10.0 g (0.06 mol) of potassium iodide in 200 ml of acetone. After a further 20 hours at reflux, 500 ml of water are added at room temperature and the mixture is then extracted with ether. The crude product is worked up in customary manner, excess benzyl chloride is removed by distillation, and the residue is recrystallised from hexane/ethyl acetate. Colourless crystals, yield 45.0 g (98% of theory)

Workup

  1. temperatureAfter a further 20 hours at reflux
  2. extractionthe mixture is then extracted with ether
  3. customis removed by distillation
  4. customthe residue is recrystallised from hexane/ethyl acetate

Sources & evidence

ORD record
ord-f43d1b06d27048deb2ae55e3779fe78c
Source dataset
uspto-grants-2005_01
Patent number
US06846492B2

Reaction notes

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