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

HRID 1894917Notes

Reaction equation

HRID 1894917 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+]>CS(C)=O.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

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Methyl 3,4,5-trihydroxybenzoate (16) (55.24 g, 0.3 mol), benzyl chloride (113.93 g, 0.9 mol), potassium carbonate (124.39 g, 0.9 mol) and potassium iodide (catalytic amount) were mechanically stirred in dry DMSO (200 mL) at room temperature overnight. Water (200 mL) was added and the crude product isolated by filtration. Evaporation of residual solvents in a vacuum desiccator left a pale yellow solid which was essentially pure product. Yield: 128.2 g (94%).

Sources & evidence

ORD record
ord-219ffa79c37442519ff32485584c469d
Source dataset
uspto-grants-2013_08
Patent number
US08513395B2

Reaction notes

Loading…