Potassium Hydroxide → 1,3-Benzenedicarboxylic acid, 5-(2-phenylethynyl)-, potassium salt (1:2)

HRID 498158Notes

Reaction equation

HRID 498158 reaction equation
[OH-].[K+:2].C[O:4][C:5]([C:7]1[CH:8]=[C:9]([C:17]#[C:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:10]=[C:11]([C:13]([O:15]C)=[O:14])[CH:12]=1)=[O:6]>C(O)CCC>[C:19]1([C:18]#[C:17][C:9]2[CH:10]=[C:11]([C:13]([O-:15])=[O:14])[CH:12]=[C:7]([CH:8]=2)[C:5]([O-:6])=[O:4])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[K+:2].[K+:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 10946313dimethyl 5-phenylethynylisophthalate

Product 1

HCID 120809071,3-Benzenedicarboxylic acid, 5-(2-phenylethynyl)-, potassium salt (1:2)Yield 97%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Into a 5 liter four-necked flask equipped with a thermometer, a Dimroth condenser and a stirrer, 3 liters of n-butanol and 180 g (2.72 moles) of potassium hydroxide (85%) were placed and dissolved by heating under the refluxing condition. To the obtained solution, 80 g (0.272 moles) of (3,5-bis(methoxycarbonyl)phenyl)-2-phenylethyne synthesized above was added and the resultant mixture was heated for 30 minutes under the refluxing condition. The reaction mixture was then cooled in an ice bath and the formed crystals were separated by filtration. The crystals were washed twice with 1 liter of ethanol and dried at 60° C. under a reduced pressure and 90.35 g of dipotassium 5-(2-phenylethynyl)-isophthalate was obtained (the yield: 97%).

Workup

  1. customInto a 5 liter four-necked flask equipped with a thermometer
  2. dissolutiondissolved
  3. temperatureby heating under the refluxing condition
  4. additionabove was added
  5. temperatureThe reaction mixture was then cooled in an ice bath
  6. customthe formed crystals were separated by filtration
  7. washThe crystals were washed twice with 1 liter of ethanol
  8. customdried at 60° C. under a reduced pressure

Sources & evidence

ORD record
ord-c447c8e6758a4491975f397b5169b8e7
Source dataset
uspto-grants-2005_09
Patent number
US06949674B2

Reaction notes

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