Sodium Iodide → HCID 9012670, compound

HRID 982900Notes

Reaction equation

HRID 982900 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].[OH:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O>[C:18]([C:17]1[CH:20]=[CH:21][C:14]([O:13][CH2:2][C:3]2[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=2)[C:6]([O:8][CH3:9])=[O:7])=[CH:15][CH:16]=1)#[N:19]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 130194-CyanophenolHCID 517981Methyl 3-(bromomethyl)benzoate

Product 1

HCID 9012670HCID 9012670, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
20 °C

Procedure

10.00 kg (43.6 mol) of methyl 3-(bromomethyl)benzoate and 5.21 kg (43.74 mol) of 4-hydroxybenzonitrile are dissolved in 100 litres of acetone and stirred with 8.4 kg (60.7 mol) of potassium carbonate in the presence of 0.1 kg of sodium iodide for about 4 h under reflux conditions. Then 35 litres of acetone are distilled off and 100 litres of water are added at reflux conditions. The reaction mixture is cooled to 20° C. and the crystallisation is completed by the addition of another 30 litres of water. The crystals formed are separated off, washed with 50 litres of water and dried in vacuo.

Workup

  1. distillationThen 35 litres of acetone are distilled off
  2. addition100 litres of water are added
  3. temperatureat reflux conditions
  4. customthe crystallisation
  5. additionis completed by the addition of another 30 litres of water
  6. customThe crystals formed
  7. customare separated off
  8. washwashed with 50 litres of water
  9. customdried in vacuo

Sources & evidence

ORD record
ord-a6c5fb64293f479d988da6231814599d
Source dataset
uspto-grants-2005_03
Patent number
US06861547B2

Reaction notes

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