Dicyclohexylcarbodiimide → Benzophenone

HRID 335048Notes

Reaction equation

HRID 335048 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.[C:16]([C:24]1[CH:34]=[CH:33][C:27](OCC(O)=O)=[CH:26][CH:25]=1)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC(N(C)C)=O>[C:16]([C:24]1[CH:34]=[CH:33][CH:27]=[CH:26][CH:25]=1)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 806092-(4-Benzoylphenoxy)acetic acid

Product 1

HCID 3102BenzophenoneYield 68.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
0 °C

Procedure

8 g of a hyperbranched polyglycidol with an average molecular weight 2000, prepared according to W02000/37532 (Bayer A.-G.) and Sunder A. et al, Macromolecules, 32, 4240-4246 (1999), was dissolved in 200 mL dimethyl acetamide at 40° C. 12.9 g (62 mmol) DCC was added and the mixture was stirred for 30 minutes. 13.3 g (52 mmol) 2-(4-benzoylphenoxy)-acetic acid was added and the reaction was allowed to continue for 16 hours at 60° C. The precipitated DCU was removed by filtration and the solvent was evaporated under reduced pressure. The residue was treated with 150 mL dichloromethane and the mixture was cooled to 0° C. After one hour, precipitated DCU was removed by filtration and the solvent was evaporated under reduced pressure. The benzophenone substituted hyperbranched polyglycidol was purified by preparative size exclusion chromatography on a 60×2.5 cm column, PL-gel 10 micron, pore size=500 A, Mw range: 500-30000, supplied by Polymer Laboratories, using tetrahydrofurane, 5% acetic acid as eluent at a flow rate of 10 mL/min and a product load of 200 mg per run. The pooled fractions were evaporated under reduced pressure. The residue was redissolved in 1000mL methylene chloride, extracted with 500 mL brine, dried over MgSO4 and the solvent was removed under reduced pressure. 6.5 g of the benzophenone substituted polyglycidol was isolated. 1H-NMR-analysis showed that the isolated polymer was substituted with 7 benzophenone moieties on average.

Workup

  1. custom8 g of a hyperbranched polyglycidol with an average molecular weight 2000, prepared
  2. waitto continue for 16 hours at 60° C
  3. customThe precipitated DCU was removed by filtration
  4. customthe solvent was evaporated under reduced pressure
  5. additionThe residue was treated with 150 mL dichloromethane
  6. waitAfter one hour
  7. customprecipitated DCU
  8. customwas removed by filtration
  9. customthe solvent was evaporated under reduced pressure
  10. customThe benzophenone substituted hyperbranched polyglycidol was purified by preparative size exclusion chromatography on a 60×2.5 cm column, PL-gel 10 micron, pore size=500 A, Mw range
  11. customThe pooled fractions were evaporated under reduced pressure
  12. dissolutionThe residue was redissolved in 1000mL methylene chloride
  13. extractionextracted with 500 mL brine
  14. dry with materialdried over MgSO4
  15. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b2cbf765dd19493cb6bcf9f2ef68d16e
Source dataset
uspto-grants-2014_11
Patent number
US08883873B2

Reaction notes

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