Potassium Carbonate → HCID 25918691, compound

HRID 491820Notes

Reaction equation

HRID 491820 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9])#[N:2].Br[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:15]([O:14][C:12](=[O:13])[CH2:11][O:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:1]#[N:2])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 119072-HydroxybenzonitrileHCID 79177tert-Butyl bromoacetate

Product 1

HCID 25918691HCID 25918691, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Cyanophenol (107.1 g) is dissolved in acetone (1000 ml) and is added t-butyl bromoacetate (200.0 g). Furthermore, potassium carbonate (141.6 g) is added, and then the reaction solution is heated under reflux for 2 hours. After allowing to cool, the insoluble materials are removed by filtration, and then the insoluble materials are washed with acetone several times. The filtrate and the washing are combined, concentrated under reduced pressure and treated with diisopropyl ether azeotropically. The resulting residue is crystallized from n-hexane-diisopropyl ether (5/1) (600 ml), and then stirred under ice-cooling. The precipitates are collected by filtration, washed with cold n-hexane-diisopropyl ether (10/1) (600 ml) several times and dried to give the title compounds (194.5 g).

Workup

  1. temperaturethe reaction solution is heated
  2. temperatureunder reflux for 2 hours
  3. temperatureto cool
  4. customthe insoluble materials are removed by filtration
  5. washthe insoluble materials are washed with acetone several times
  6. concentrationconcentrated under reduced pressure
  7. additiontreated with diisopropyl ether azeotropically
  8. customThe resulting residue is crystallized from n-hexane-diisopropyl ether (5/1) (600 ml)
  9. temperaturecooling
  10. filtrationThe precipitates are collected by filtration
  11. washwashed with cold n-hexane-diisopropyl ether (10/1) (600 ml) several times
  12. customdried

Sources & evidence

ORD record
ord-61cc421a011543f08c62f05a1cd880b6
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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