Azobisisobutyronitrile → 7'-bromo-2'-ethyl-6',9',11'-trihydroxyspiro[1,3-dioxolane-2,1'-7,8,9,10-tetrahydro-2H-tetracene]-5',12'-dione

HRID 64902Notes

Reaction equation

HRID 64902 reaction equation
[CH2:1]1[CH2:29][O:28][C:3]2([C:20]3[C:19](=[O:21])[C:18]4[C:9](=[C:10]([OH:24])[C:11]5[CH2:12][CH2:13][CH:14]([OH:23])[CH2:15][C:16]=5[C:17]=4[OH:22])[C:8](=[O:25])[C:7]=3[CH:6]=[CH:5][CH:4]2[CH2:26][CH3:27])[O:2]1.N(C(C)(C)C#N)=NC(C)(C)C#N.[Br:42]Br>C(Cl)(Cl)Cl.C(Cl)(Cl)(Cl)Cl.O>[Br:42][CH:12]1[CH2:13][CH:14]([OH:23])[CH2:15][C:16]2[C:17]([OH:22])=[C:18]3[C:9]([C:8](=[O:25])[C:7]4[CH:6]=[CH:5][CH:4]([CH2:26][CH3:27])[C:3]5([O:2][CH2:1][CH2:29][O:28]5)[C:20]=4[C:19]3=[O:21])=[C:10]([OH:24])[C:11]1=2

Participants

7

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 24408BromineHCID 131714852HCID 131714852, compound

Product 1

HCID 1784355427'-bromo-2'-ethyl-6',9',11'-trihydroxyspiro[1,3-dioxolane-2,1'-7,8,9,10-tetrahydro-2H-tetracene]-5',12'-dione

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolventHCID 6212ChloroformSolvent

Procedure

9-(1,1-Ethylenedioxy)ethyl-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione (10.0 g) was dissolved in a mixture of chloroform (395 ml), carbon tetrachloride (980 ml) and water (890 ml) while heating, azobisisobutyronitrile (2.0 g) and bromine (8.0 g) were added thereto in order, and the resultant mixture was stirred under reflux for 1.5 hours. The reaction mixture was stirred in an ice bath for 1 hour, and the precipitated red orange crystals were collected by filtration, washed with water and dried under reduced pressure to give the crude product of 7-bromo-9-(1,1-ethylenedioxy)ethyl-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione. M.P., 196°-235° C.; IR (Nujol) ν cm-1 : 3550, 1625, 1590. This product was used as such in the following step without purification.

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux for 1.5 hours
  3. filtrationthe precipitated red orange crystals were collected by filtration
  4. washwashed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-920b6fd6f4d24ab99b353d27ce1c8e92
Source dataset
uspto-grants-1986_09
Patent number
US04610986

Reaction notes

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