Methanol → HCID 86640905, compound

HRID 2192761Notes

Reaction equation

HRID 2192761 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1.[OH2:14].ON1[C:20]2C=CC=C[C:19]=2N=N1.[CH2:25](N(CC)CC)[CH3:26].[CH3:32]O>CN(C=O)C>[CH:3]12[CH2:7][CH:6]([CH:5]=[CH:4]1)[CH2:12][CH:13]2[CH2:32][OH:14].[CH2:19]=[CH2:20].[CH:3]12[CH2:7][CH:6]([CH:5]=[CH:4]1)[CH2:12][CH2:13]2.[CH3:25][C:12]1[CH:13]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=1[CH:7]=[CH:8][C:9]([O-:11])=[O:10].[CH2:25]=[CH2:26]

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 132454-Methoxy cinnamic acidHCID 27960291-Hydroxybenzotriazole hydrate

Product 2

HCID 86640905HCID 86640905, compoundHCID 86640906HCID 86640906, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The 5-norbornene-2-methanol/ethylene copolymer (18.4 g, 0.121 mol) that was polymerized in (2), 4-methoxy cinnamic acid (Aldrich, 21.5 g, 0.121 mol), EDC [1-(3-dimethylaminopropyl)-3-ethylcarboimide hydrochloride] (Aldrich, 37 g, 0.194 mol), and HOBT (1-hydroxybenzotriazole hydrate) (Aldrich, 24.5 g, 0.182 mol) were put into the 2-neck flask having the volume of 250 ml, and then dissolved in 100 ml of DMF. After the temperature was reduced to 0° C., triethylamine (Aldrich, 75 ml, 0.605 mol) was slowly dropped on the reaction solution. After the temperature was increased to normal temperature and maintained for 3 hours, when the reaction was finished, the reaction solution was dropped on a large amount of methanol to precipitate the polymer, and the polymer was filtered to obtain the 5-norbornene-2-methyl-(4-methoxy cinnamate)/ethylene copolymer to which the 4-methoxy cinnamoyl functional group was introduced (yield: 90.5%).

Workup

  1. customwas reduced to 0° C.
  2. temperatureAfter the temperature was increased to normal temperature
  3. temperaturemaintained for 3 hours
  4. customto precipitate the polymer
  5. filtrationthe polymer was filtered

Sources & evidence

ORD record
ord-7ed2a3ca1a5f433f9f60c3afc76329bb
Source dataset
uspto-grants-2012_12
Patent number
US08329841B2

Reaction notes

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