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

HRID 340871
Notes
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Reaction equation

HRID 340871 reaction equation
[OH:1][CH2:2][C:3]([O:5][C:6]([CH3:18])([CH2:8][CH2:9][C:10]([O:13][C:14](=[O:17])[CH2:15][OH:16])([CH3:12])[CH3:11])[CH3:7])=[O:4].[C:19]([Cl:30])(=[O:29])[C:20]1[CH:28]=[CH:27][CH:26]=[C:22]([C:23]([Cl:25])=[O:24])[CH:21]=1.[C:31]([O:34][C:35]1[CH:36]=[C:37]([C:44]([Cl:46])=[O:45])[CH:38]=[C:39]([CH:43]=1)[C:40]([Cl:42])=[O:41])(=[O:33])[CH3:32].N12CCN(CC1)CC2.[I-].[K+].C(O)(O)CCC>N1C=CC=CC=1>[OH:1][CH2:2][C:3]([O:5][C:6]([CH3:18])([CH2:8][CH2:9][C:10]([O:13][C:14](=[O:17])[CH2:15][OH:16])([CH3:11])[CH3:12])[CH3:7])=[O:4].[C:23]([Cl:25])(=[O:24])[C:22]1[CH:26]=[CH:27][CH:28]=[C:20]([C:19]([Cl:30])=[O:29])[CH:21]=1.[C:31]([O:34][C:35]1[CH:43]=[C:39]([C:40]([Cl:42])=[O:41])[CH:38]=[C:37]([CH:36]=1)[C:44]([Cl:46])=[O:45])(=[O:33])[CH3:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 6

HCID 4875Potassium IodideHCID 7451Isophthaloyl chlorideHCID 9237DabcoHCID 165788ButanediolHCID 105155301,3-Benzenedicarbonyl dichloride, 5-(acetyloxy)-HCID 582821182,5-Dimethylhexane-2,5-diyl bis(2-hydroxyacetate)

Product 1

HCID 131732089
2,5-Dimethylhexane-2,5-diyl bis(2-hydroxyacetate) isophthaloyl chloride 5-acetoxy isophthaloyl chloride

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 2,5-dimethylhexane-2,5-diyl bis(2-hydroxyacetate) (69) (0.997 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 ˜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-166246f5cd0945e6994ee866b8329084
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08895691B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes