Potassium Iodide → (E)-Hex-3-ene-2,5-diol isophthaloyl chloride 5-acetoxy isophthaloyl chloride

HRID 340875Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 340875
[CH3:1][CH:2]([OH:8])/[CH:3]=[CH:4]/[CH:5]([OH:7])[CH3:6].[C:9]([Cl:20])(=[O:19])[C:10]1[CH:18]=[CH:17][CH:16]=[C:12]([C:13]([Cl:15])=[O:14])[CH:11]=1.[C:21]([O:24][C:25]1[CH:26]=[C:27]([C:34]([Cl:36])=[O:35])[CH:28]=[C:29]([CH:33]=1)[C:30]([Cl:32])=[O:31])(=[O:23])[CH3:22].N12CCN(CC1)CC2.[I-].[K+].C(O)(O)CCC>N1C=CC=CC=1>[CH3:1][CH:2]([OH:8])/[CH:3]=[CH:4]/[CH:5]([OH:7])[CH3:6].[C:13]([Cl:15])(=[O:14])[C:12]1[CH:16]=[CH:17][CH:18]=[C:10]([C:9]([Cl:20])=[O:19])[CH:11]=1.[C:21]([O:24][C:25]1[CH:33]=[C:29]([C:30]([Cl:32])=[O:31])[CH:28]=[C:27]([CH:26]=1)[C:34]([Cl:36])=[O:35])(=[O:23])[CH3:22]

Komponenten

8

Edukt 6

HCID 4875Potassium IodideHCID 7451Isophthaloyl chlorideHCID 9237DabcoHCID 165788ButanediolHCID 53632993-Hexene-2,5-diolHCID 105155301,3-Benzenedicarbonyl dichloride, 5-(acetyloxy)-

Produkt 1

HCID 131732093(E)-Hex-3-ene-2,5-diol isophthaloyl chloride 5-acetoxy isophthaloyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel2×

Versuchsvorschrift

A solution of (E)-hex-3-ene-2,5-diol (122) (0.441 g, 3.8 mmol), isophthaloyl chloride (115) (0.406 g, 2.0 mmol), 5-acetoxy isophthaloyl chloride (117) (0.522 g, 2.0 mmol), a catalytic amount of 1,4-diazabicyclo[2.2.2]octane, and a catalytic amount of potassium iodide in 20 mL of pyridine was brought to 50° C. while stirring under nitrogen. After 24 hours, butanediol (0.072 g, 0.8 mmol) diluted in 10 mL of pyridine was added to the reaction mixture using a syringe pump over 8 hours. The solution was then quenched in 200 mL of cold 1N hydrochloric acid. The polymer precipitate is collected by filtration, redissolved in tetrahydrofuran, and precipitated in 100 mL of cold 1N hydrochloric acid. The polymer is then collected by filtration and dried under high vacuum. The polymer was found to have a molecular weight of ˜12,000 g/mol by GPC.

Aufarbeitung

  1. customwas brought to 50° C.
  2. additionwas added to the reaction mixture
  3. customover 8 hours
  4. customThe solution was then quenched in 200 mL of cold 1N hydrochloric acid
  5. filtrationThe polymer precipitate is collected by filtration
  6. dissolutionredissolved in tetrahydrofuran
  7. customprecipitated in 100 mL of cold 1N hydrochloric acid
  8. filtrationThe polymer is then collected by filtration
  9. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-e5e170c0b4a14c0d89717d6da1f7eab3
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895691B2

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