Chloranil → Hydroquinone

HRID 1448477Notes

Reaction equation

HRID 1448477 reaction equation
[C:1]1([Cl:12])[C:7](=[O:8])[C:6]([Cl:9])=[C:5]([Cl:10])[C:3](=[O:4])[C:2]=1[Cl:11]>C(O)(C)(C)C>[C:3]1([CH:5]=[CH:6][C:7]([OH:8])=[CH:1][CH:2]=1)[OH:4].[C:6]1([Cl:9])[C:7](=[O:8])[C:1]([Cl:12])=[C:2]([Cl:11])[C:3](=[O:4])[C:5]=1[Cl:10]

Participants

4

Reactant 1

HCID 8371Chloranil

Product 2

HCID 785HydroquinoneHCID 8371Chloranil

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

10.0 g. of 17α-hydroxy-15α,16α-methylene-17α-[3-(tetrahydropyran-2-yloxy)propyl]-4-androsten-3-one is heated under reflux in 100 ml. of tert.-butanol with 10.0 g. of chloranil for 18 hours. The mixture is filtered off from the precipitate, which has formed (hydroquinone and unreacted chloranil); the filtrate is diluted with ether, washed with sodium bicarbonate solution and water, dried, and evaporated, thus obtaining 10 g. of crude 17β-hydroxy-15α, 16α-methylene-17α-[3-(tetrahydropyran-2-yloxy)propyl]-4,6-androstadien-3-one.

Workup

  1. temperatureunder reflux in 100 ml
  2. filtrationThe mixture is filtered off from the precipitate

Sources & evidence

ORD record
ord-5a1d0af03c2a43eeb2eaa2fc8e264a86
Source dataset
uspto-grants-1979_12
Patent number
US04180570

Reaction notes

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