Ammonia → (E)-Hex-3-ene-2,5-diol isophthaloyl chloride 5-hydroxyisophthaloyl dichloride

HRID 340876Notes

Reaction equation

HRID 340876 reaction equation
N.[CH3:2][CH:3]([OH:9])/[CH:4]=[CH:5]/[CH:6]([OH:8])[CH3:7].[C:10]([Cl:21])(=[O:20])[C:11]1[CH:19]=[CH:18][CH:17]=[C:13]([C:14]([Cl:16])=[O:15])[CH:12]=1.C([O:25][C:26]1[CH:27]=[C:28]([C:35]([Cl:37])=[O:36])[CH:29]=[C:30]([CH:34]=1)[C:31]([Cl:33])=[O:32])(=O)C>O1CCCC1>[CH3:2][CH:3]([OH:9])/[CH:4]=[CH:5]/[CH:6]([OH:8])[CH3:7].[C:14]([Cl:16])(=[O:15])[C:13]1[CH:17]=[CH:18][CH:19]=[C:11]([C:10]([Cl:21])=[O:20])[CH:12]=1.[OH:25][C:26]1[CH:34]=[C:30]([C:31]([Cl:33])=[O:32])[CH:29]=[C:28]([CH:27]=1)[C:35]([Cl:37])=[O:36]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 131732093(E)-Hex-3-ene-2,5-diol isophthaloyl chloride 5-acetoxy isophthaloyl chloride

Product 1

HCID 131732094(E)-Hex-3-ene-2,5-diol isophthaloyl chloride 5-hydroxyisophthaloyl dichloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methanolic ammonia (20 mL, 1 N), polymer (124) dissolved in 5 mL tetrahydrofuran is added and the solution is stirred for two hours. The polymer was then precipitated in 100 mL of cold 1 N hydrochloric acid and collected by filtration. The polymer was then dried under high vacuum and was found to have a molecular weight of ˜5,000 g/mol by GPC.

Workup

  1. additionis added
  2. customThe polymer was then precipitated in 100 mL of cold 1 N hydrochloric acid
  3. filtrationcollected by filtration
  4. customThe polymer was then dried under high vacuum

Sources & evidence

ORD record
ord-57832659b5c64dbe8dc2d4780081146f
Source dataset
uspto-grants-2014_11
Patent number
US08895691B2

Reaction notes

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