Benzene → HCID 13020861, compound

HRID 262965Notes

Reaction equation

HRID 262965 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C@H:11]([CH2:12][C:13](=[O:22])[CH2:14][C@@H:15]1[CH3:21])[CH2:10][CH2:9]3.C1(C)C=CC(S(O)(=O)=[O:30])=CC=1.[CH:34]1[CH:39]=CC=CC=1>CCOCC>[CH2:34]1[CH2:39][O:30][C:13]2([CH2:14][C@H:15]([CH3:21])[C@@:16]3([CH3:17])[C@@H:11]([CH2:10][CH2:9][C@@H:8]4[C@@H:18]3[CH2:19][CH2:20][C@@:3]3([CH3:4])[C@H:5]4[CH2:6][CH2:7][C@@H:2]3[OH:1])[CH2:12]2)[O:22]1

Participants

5

Reactant 3

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 15020Mesterolone

Product 1

HCID 13020861HCID 13020861, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

50 g of 17β-hydroxy-1α-methyl-5α-androstan-3-one were heated at reflux in 1000 ml of absolute benzene, 125 ml of ethylenegycol and 1.25 g of p-toluenesulphonic acid for 7 hours while stirring under a water separator. The solution was then diluted with ether, washed with sodium hydrogen carbonate solution and water, dried and evaporated to dryness. 55 g of 3,3-ethylenedioxy-17β-hydroxy-1α-methyl-5α-androstane were obtained.

Workup

  1. washwashed with sodium hydrogen carbonate solution and water
  2. customdried
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-c270b92b3b3f42d28205ea31f459b52a
Source dataset
uspto-grants-1979_05
Patent number
US04155918

Reaction notes

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