Sodium Iodide → HCID 53645944, compound

HRID 2256700Notes

Reaction equation

HRID 2256700 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+]>CC(C)=O>[CH2:15]([O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:10][C:2]=1[O:1][CH2:4][C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:2]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 4330244-tert-Butyl-2-hydroxybenzoic acid

Product 1

HCID 53645944HCID 53645944, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5 g of 2-hydroxy-4-tert-butyl-benzoic acid, 9.1 ml of benzyl bromide, 17 g of caesium carbonate, 0.3 g of sodium iodide and 500 ml of acetone is stirred for 20 hours under reflux and then filtered and the filtrate is concentrated by evaporation. The residue is partitioned between diethyl ether and water, the organic phases are concentrated by evaporation and the residue is purified by means of FC (1000 g of silica gel, dichloromethane/hexane=1:1). Title compound: Rf (dichloromethane/hexane=1:1)=0.47.

Workup

  1. temperatureunder reflux
  2. filtrationfiltered
  3. concentrationthe filtrate is concentrated by evaporation
  4. customThe residue is partitioned between diethyl ether and water
  5. concentrationthe organic phases are concentrated by evaporation
  6. customthe residue is purified by means of FC (1000 g of silica gel, dichloromethane/hexane=1:1)

Sources & evidence

ORD record
ord-e1283558dc244659b5c97c5592c59d92
Source dataset
uspto-grants-1997_08
Patent number
US05654445

Reaction notes

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