Sodium Iodide → HCID 9012670, compound

HRID 2228839Notes

Reaction equation

HRID 2228839 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 liters 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 liters of acetone are distilled off and 100 liters 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 liters of water. The crystals formed are separated off, washed with 50 liters of water and dried in vacuo.

Workup

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

Sources & evidence

ORD record
ord-6962ba060d764e369c18e8c554ff5222
Source dataset
uspto-grants-2002_07
Patent number
US06417382B1

Reaction notes

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