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

HRID 340874

Reaction equation

HRID 340874 reaction equation
[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.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

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 7451Isophthaloyl chlorideHCID 9237DabcoHCID 165788ButanediolHCID 53632993-Hexene-2,5-diol

Product 1

HCID 86654796(E)-Hex-3-ene-2,5-diol isophthaloyl chloride

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of (E)-hex-3-ene-2,5-diol (122) (0.441 g, 3.8 mmol), isophthaloyl chloride (115) (0.812 g, 4.0 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 cold 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.

Workup

  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 cold 100 mL of cold 1N hydrochloric acid
  8. filtrationThe polymer is then collected by filtration
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-9caa998c7a48495b85cd7f915d1f50f5
Source dataset
uspto-grants-2014_11
Patent number
US08895691B2

Linked notes

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