Methanol → Diisopropyl fumarate cinnamic acid

HRID 634040

Reaction equation

HRID 634040 reaction equation
[C:1]([O:11][CH:12]([CH3:14])[CH3:13])(=[O:10])/[CH:2]=[CH:3]/[C:4]([O:6][CH:7]([CH3:9])[CH3:8])=[O:5].[C:15]([OH:25])(=[O:24])[CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CO>O1CCCC1.C(OOC(C)(C)C)(=O)C(C)(C)C>[C:4]([O:6][CH:7]([CH3:9])[CH3:8])(=[O:5])/[CH:3]=[CH:2]/[C:1]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10].[C:15]([OH:25])(=[O:24])[CH:16]=[CH:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 87842-Propenoic acid, 3-phenyl-HCID 5357078Diisopropyl fumarate

Product 1

HCID 118090912Diisopropyl fumarate cinnamic acidYield 123.9%

Reagents, catalysts & solvents 2

HCID 61238tert-BUTYL PEROXYPIVALATECatalystHCID 8028TetrahydrofuranSolvent

Procedure

A glass ampule having a volume of 75 mL was charged with 50 g (0.25 mol) of diisopropyl fumarate, 6.5 g (0.044 mol) of cinnamic acid and 0.32 g (0.0018 mol) of tert-butyl peroxypivalate as a polymerization initiator and after repeating purging with nitrogen and release of the pressure, sealed in the pressure-reduced state. This ampule was placed in a constant temperature bath at 50° C. and held for 48 hours, thereby performing radical polymerization. After the completion of polymerization reaction, the polymerization product was taken out of the ampule and dissolved in 400 g of tetrahydrofuran. The resulting polymer solution was added dropwise, for precipitation, to 3 L of methanol, and the precipitate was vacuum-dried at 80° C. for 10 hours to obtain 19 g of a diisopropyl fumarate/cinnamic acid copolymer (yield: 34%).

Workup

  1. customafter repeating purging with nitrogen and release of the pressure
  2. customsealed in the pressure-reduced state
  3. customThis ampule was placed in a constant temperature bath at 50° C.
  4. custompolymerization
  5. customAfter the completion of polymerization reaction
  6. customthe precipitate was vacuum-dried at 80° C. for 10 hours

Sources & evidence

ORD record
ord-57f9cfd210af468c8fb8810ca78aee08
Source dataset
uspto-grants-2016_04
Patent number
US09321870B2

Linked notes

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