Acetone → 7-Hydroxycoumarin-4-acetic acid

HRID 2051456Notes

Reaction equation

HRID 2051456 reaction equation
C[C:2]([CH3:4])=[O:3].C1(N=C=NC2CCCCC2)CCCCC1.CN(C1C=CC=CN=1)C.[CH:29]1[C:34]([OH:35])=[CH:33][C:32]2[O:36][C:37]([CH:39]=[CH:40][C:31]=2[CH:30]=1)=[O:38].C1C[O:44]CC1>>[CH:29]1[C:34]([OH:35])=[CH:33][C:32]2[O:36][C:37]([CH:39]=[C:40]([CH2:4][C:2]([OH:44])=[O:3])[C:31]=2[CH:30]=1)=[O:38]

Participants

6

Reactant 5

HCID 180AcetoneHCID 8028Tetrahydrofuran2×HCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 5281426Umbelliferone

Product 1

HCID 53384907-Hydroxycoumarin-4-acetic acidYield 69%

Procedure

20.0 g of poly(HEMA4.0 -MMA1) was dissolved in 500 cc THF plus acetone (3:2) at boiling (60° C.). 0.271 g CMU was added and stirred until dissolved. 0.245 g dicyclohexylcarbodiimide and 25 mg dimethylaminopyridine, each dissolved in THF, were added and the solution stirred for 3 hours at boiling (60° C.). The reaction solution was then work-up as described for i., giving a limegreen powder, weight 13.81 g (69% yield) of poly(HEMA4.0 -MMA1) with a theoretical molar substitution of 0.96% umbelliferone on HEMA monomer. Actual substitution was 0.53%.

Workup

  1. custom(60° C.)
  2. addition0.271 g CMU was added
  3. dissolutionuntil dissolved
  4. additionwere added
  5. stirringthe solution stirred for 3 hours
  6. custom(60° C.)
  7. custom, giving a limegreen powder, weight 13.81 g (69% yield) of poly(HEMA4.0

Sources & evidence

ORD record
ord-cb13229ccca548468e966ef2628d77aa
Source dataset
uspto-grants-1991_05
Patent number
US05019350

Reaction notes

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