Potassium Iodide → 2,5-Dimethylhexane-2,5-diylbis(2-hydroxyacetate) 5-acetoxy isophthaloyl chloride

HRID 340873Notes

Reaction equation

HRID 340873 reaction equation
[CH3:1][C:2]([CH:14]([OH:18])[C:15]([O-:17])=[O:16])([CH2:4][CH2:5][C:6]([CH3:13])([CH:8]([OH:12])[C:9]([O-:11])=[O:10])[CH3:7])[CH3:3].[C:19]([O:22][C:23]1[CH:24]=[C:25]([C:32]([Cl:34])=[O:33])[CH:26]=[C:27]([CH:31]=1)[C:28]([Cl:30])=[O:29])(=[O:21])[CH3:20].N12CCN(CC1)CC2.[I-].[K+].C(O)(O)CCC>N1C=CC=CC=1>[CH3:13][C:6]([CH:8]([OH:12])[C:9]([O-:11])=[O:10])([CH2:5][CH2:4][C:2]([CH3:1])([CH:14]([OH:18])[C:15]([O-:17])=[O:16])[CH3:3])[CH3:7].[C:19]([O:22][C:23]1[CH:31]=[C:27]([C:28]([Cl:30])=[O:29])[CH:26]=[C:25]([CH:24]=1)[C:32]([Cl:34])=[O:33])(=[O:21])[CH3:20]

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 9237DabcoHCID 165788ButanediolHCID 105155301,3-Benzenedicarbonyl dichloride, 5-(acetyloxy)-HCID 1317320922,5-Dimethylhexane-2,5-diylbis(2-hydroxyacetate)

Product 1

HCID 1317320912,5-Dimethylhexane-2,5-diylbis(2-hydroxyacetate) 5-acetoxy isophthaloyl chloride

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 2,5-dimethylhexane-2,5-diylbis(2-hydroxyacetate) (69) (0.997 g, 3.8 mmol), 5-acetoxy isophthaloyl chloride (117) (1.044 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 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 ˜14,000 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 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-421ca47d9823451abdd96ddb16de482c
Source dataset
uspto-grants-2014_11
Patent number
US08895691B2

Reaction notes

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