Acetone → HCID 67420429, compound

HRID 1594953Notes

Reaction equation

HRID 1594953 reaction equation
[CH3:1][C:2]([CH3:4])=[O:3].C(=O)([O-])[O-].[K+].[K+].[CH:11](I)([CH3:13])[CH3:12].[CH:15]([O:18][CH:19]([CH3:21])[CH3:20])([CH3:17])[CH3:16]>C#CC1C=CC(O)=CC=1.C(C(C)=O)C(C)C>[OH:3][C:2]1[CH:4]=[CH:13][C:11]([CH:15]=[CH2:16])=[CH:12][CH:1]=1.[CH:15]([O:18][C:19]1[CH:21]=[CH:4][C:2]([CH:11]=[CH2:12])=[CH:1][CH:20]=1)([CH3:17])[CH3:16]

Participants

7

Reactant 4

HCID 180AcetoneHCID 6362Isopropyl iodideHCID 7914Diisopropyl EtherHCID 11430Potassium Carbonate

Product 1

HCID 67420429HCID 67420429, compound

Reagents, catalysts & solvents 2

HCID 7909Methyl Isobutyl KetoneSolventHCID 327584-EthynylphenolSolvent2×

Procedure

Into a reaction vessel were charged 30.0 parts of the same poly(p-vinylphenol) as that used in Example 1 and 120 parts of acetone. They were stirred to form a solution. Additionally charged were 29.6 parts of anhydrous potassium carbonate and 18.2 parts of isopropyl iodide. The temperature was elevated so that the mixture reached to the lo reflux state. Subsequently, the reflux state was kept for 27 hours. After adding methyl isobutyl ketone, the solution was washed with aqueous oxalic acid solution and then with ion-exchanged water. The organic layer after washing was concentrated to 71 parts, combined with 206 parts of propylene glycol monomethyl ether acetate and further concentrated to 88.6 parts. The solid content of the concentrate measured by weight-loss on heating was 31.92% by weight. By 1H-NMR measurement, it was confirmed that the resin after reaction was a copolymer In which 31.4% of hydroxyl groups in poly(p-vinylphenol) was converted to isopropyl ether. The resin was referred to as Resin RA.

Workup

  1. customto form a solution
  2. additionAdditionally charged
  3. temperaturereflux state
  4. washthe solution was washed with aqueous oxalic acid solution
  5. washThe organic layer after washing
  6. concentrationwas concentrated to 71 parts
  7. concentrationfurther concentrated to 88.6 parts
  8. temperatureon heating
  9. customafter reaction

Sources & evidence

ORD record
ord-a80dda4271604fccae229c5d9ba600f4
Source dataset
uspto-grants-2001_09
Patent number
US06284863B1

Reaction notes

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