HCID 13565763, compound → HCID 13984538, compound

HRID 477908Notes

Reaction equation

HRID 477908 reaction equation
[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[OH:17])[CH:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1>C(OC(=O)CC)(=O)CC.N1C=CC=CC=1>[C:18]1([C:7]2[C:6]3[C:15](=[C:2]([O:1][C:12](=[O:17])[CH2:11][CH3:10])[CH:3]=[CH:4][CH:5]=3)[C:14]([O:16][C:14](=[O:16])[CH2:13][CH3:8])=[C:13]3[C:8]=2[CH:9]=[CH:10][CH:11]=[C:12]3[O:17][C:2](=[O:1])[CH2:3][CH3:4])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 1

HCID 13565763HCID 13565763, compound

Product 1

HCID 13984538HCID 13984538, compoundYield 56.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 31263Propionic anhydrideSolvent

Procedure

To a mixture, stirred under an argon atmosphere, of 2.5 g of 1,8-dihydroxy-10-phenyl anthrone obtained at example 10 (1) in 25 cm3 of propionic anhydride, 0.100 cm3 of anhydrous pyridine is added. The reaction mixture is then brought for one hour to 70° C., at the end of which period all the initial reactant is transformed. The reactive excess is then removed by evaporation under a vacuum. The resulting solid is dissolved in a minimum of toluene, introduced into a silica gel column and then eluted with toluene. After evaporation of the eluant, 1.3 g of a solid are obtained which is then recrystallized in a toluene/hexane mixture, yielding 1.1 g white crystals having a melting point of 216° C.

Workup

  1. additionis added
  2. customThe reactive excess is then removed by evaporation under a vacuum
  3. dissolutionThe resulting solid is dissolved in a minimum of toluene
  4. additionintroduced into a silica gel column
  5. washeluted with toluene
  6. customAfter evaporation of the eluant, 1.3 g of a solid
  7. customare obtained which
  8. customis then recrystallized in a toluene/hexane mixture

Sources & evidence

ORD record
ord-60326fe669794534b62567b98ee15f6d
Source dataset
uspto-grants-1989_12
Patent number
US04889865

Reaction notes

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