Potassium Carbonate → HCID 25918691, compound

HRID 1820932Notes

Reaction equation

HRID 1820932 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:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])#[N:2]

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 thereto is added t-butyl bromoacetate (200.0 g). Potassium carbonate (141.6 g) is added, and the reaction solution is heated under reflux for 2 hours. After allowing to cool, the insoluble materials are removed by filtration, and the insolubles are washed with acetone several times. The filtrate and washings 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), followed by stirring 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 compound (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 insolubles 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-3d0941de24924241a7349de9f95e2c01
Source dataset
uspto-grants-2009_10
Patent number
US07605158B2

Reaction notes

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