Ethanol → Butyl norbornene 5-norbornene-2-carboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH:9]2[CH2:11][CH:6]1[CH:7]=[CH:8]2)=[O:4].[CH2:12]([C:16]12[CH2:22][CH:19]([CH2:20][CH2:21]1)[CH:18]=[CH:17]2)[CH2:13][CH2:14][CH3:15].C1(C)C=CC=CC=1.C(O)C>ClCCl.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Pd+2]>[CH2:12]([C:16]12[CH2:22][CH:19]([CH2:20][CH2:21]1)[CH:18]=[CH:17]2)[CH2:13][CH2:14][CH3:15].[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH:9]2[CH2:11][CH:6]1[CH:7]=[CH:8]2)=[O:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A 5-norbornene-2-carboxylic acid methyl ester monomer (14.64 g), a butyl norbornene monomer (6.14 g), and toluene (37 Ml) were added to a 250 Ml Schlenk flask. A solution of Pd(acac)2 (4.19 mg, acac=acetylacetonate) and [(Cy)3PH][B(C6F5)4] (32.8 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 a 13.7 g of butyl norbornene/5-norbornene-2-carboxylic acid methyl ester copolymer (yield: 65.9 wt % based on the total weight of the monomers). The Mw and Mw/Mn of the polymer were 157,000 and 2.13, respectively.
Workup
- customto obtain a white copolymer precipitate
- filtrationThe precipitate was filtered through a glass funnel
- customdried in a vacuum oven at 65° C. for 24 hours
Sources & evidence
- ORD record
- ord-8273cd22f9be4d26ae075455bfae2849
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07638653B2
Reaction notes
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