Ethanol → HCID 69002393, compound

HRID 1869724Notes

Reaction equation

HRID 1869724 reaction equation
[CH3:1][O:2][C:3]([C:5]12[CH2:11][CH:8]([CH2:9][CH2:10]1)[CH:7]=[CH:6]2)=[O:4].[CH:12]12[CH2:18][CH:15]([CH2:16][CH2:17]1)[CH:14]=[CH:13]2.C1(C)C=CC=CC=1.C(O)C>ClCCl.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:5]12[CH2:11][CH:8]([CH2:9][CH2:10]1)[CH:7]=[CH:6]2.[CH3:1][O:2][C:3]([CH:13]1[CH2:14][CH:15]2[CH2:18][CH:12]1[CH:17]=[CH:16]2)=[O:4]

Participants

7

Reactant 4

HCID 702EthanolHCID 1140TolueneHCID 103522-NorborneneHCID 12491640HCID 12491640, compound

Product 1

HCID 69002393HCID 69002393, compoundYield 127.9%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A norbornene carboxylic acid methyl ester monomer (16.74 g), a norbornene monomer (4.44 g), and 37 Ml of toluene were added to a 250 Ml Schlenk flask. A solution of Pd(OAc)2 (4.79 mg) and [(Cy)3PH][B(C6F5)4] (40.4 mg) in dichloromethane (2 Ml) was added to the flask, and the reaction mixture was incubated at 90° C. for 10 hours while stirring. Then, the reaction solution was added to excess ethanol to obtain a white copolymer precipitate. The precipitate was filtered through a glass funnel and dried in a vacuum oven at 65° C. for 24 hours to give 14.86 g of a norbornene/5-norbornene-2-carboxylic acid methyl ester copolymer (yield: 70.2 wt % based on the total weight of the monomers). The Mw and Mw/Mn of the polymer were 184,000 and 2.12, respectively.

Workup

  1. customto obtain a white copolymer precipitate
  2. filtrationThe precipitate was filtered through a glass funnel
  3. customdried in a vacuum oven at 65° C. for 24 hours

Sources & evidence

ORD record
ord-bf9a53aa327a4947b5dbaeeb21c7026a
Source dataset
uspto-grants-2009_12
Patent number
US07638653B2

Reaction notes

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