Acetone → 4-Ethynylphenol

HRID 1456897Notes

Reaction equation

HRID 1456897 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[I-].[K+].[C:9](OC(=O)CCl)([CH3:12])([CH3:11])[CH3:10].[CH3:18][C:19]([CH3:21])=[O:20]>>[CH:1]#[C:12][C:9]1[CH:10]=[CH:21][C:19]([OH:20])=[CH:18][CH:11]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 66052tert-Butyl chloroacetate

Product 1

HCID 327584-Ethynylphenol

Procedure

50.0 g of the resin synthesized in Reference Example 12 was dissolved in 500 ml of acetone. After adding 9.5 g of potassium carbonate, 1.9 g of potassium iodide and 8.6 g of tert-butylchloroacetate, the solution thus obtained was refluxed for 10 hours. After filtration of the reaction solution, 1 l of methylisobutylketone was mixed to the resin solution thus obtained, and the resulting solution was washed three times with 500 ml of ion-exchange water. The methylisobutylketone was distilled out under reduced pressure to obtain poly(p-vinylphenol), wherein 8% of the hydroxyl groups were ethyletherified and 14% of the hydroxyl groups were tert-butoxycarbonylmethyletherified. The weight average molecular weight of this resin is 14,800 and its molecular weight distribution is 1.28.

Workup

  1. customthe solution thus obtained
  2. temperaturewas refluxed for 10 hours
  3. filtrationAfter filtration of the reaction solution, 1 l of methylisobutylketone
  4. additionwas mixed to the resin solution
  5. customthus obtained
  6. washthe resulting solution was washed three times with 500 ml of ion-exchange water
  7. distillationThe methylisobutylketone was distilled out under reduced pressure

Sources & evidence

ORD record
ord-a6a01502c74a441e94a0077f2009f6ee
Source dataset
uspto-grants-1998_12
Patent number
US05846688

Reaction notes

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