Benzene → HCID 53997316, compound

HRID 1607974Notes

Reaction equation

HRID 1607974 reaction equation
[OH-].[K+].C([O:6][C@@H:7]1[C@@:26]2([CH3:27])[C@@H:19]([CH2:20][CH2:21][C@@H:22]2[C:23](=[O:25])[CH3:24])[C@H:18]2[C@@H:9]([C@:10]3([CH3:29])[C:15]([CH2:16][CH2:17]2)=[CH:14][C:13](=[O:28])[CH:12]=[CH:11]3)[CH2:8]1)(=O)C.C1C=CC=CC=1>CO>[OH:6][C@@H:7]1[C@@:26]2([CH3:27])[C@@H:19]([CH2:20][CH2:21][C@@H:22]2[C:23](=[O:25])[CH3:24])[C@H:18]2[C@@H:9]([C@:10]3([CH3:29])[C:15]([CH2:16][CH2:17]2)=[CH:14][C:13](=[O:28])[CH:12]=[CH:11]3)[CH2:8]1

Participants

5

Reactant 3

HCID 241BenzeneHCID 14797Potassium HydroxideHCID 54119102HCID 54119102, compound

Product 1

HCID 53997316HCID 53997316, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2.2 g of potassium hydroxide in 80 ml of methanol was added 7.4 g of 12α-acetoxypregna-1,4-diene-3,20-dione, and the mixture was stirred at room temperature for 10 hours. The reaction mixturewas concentrated to about one tenth the original volume by distilling off the methanol under reduced pressure. To the concentrated reaction mixture was added 150 ml of benzene, and the solution was washed in sequence with water, diluted hydrochloric acid and water and then dried over anhydrous magnesium sulfate. Low-boiling fractions were distilled off under reduced pressure and the residue was recrystallized from ethyl acetate to give 5.4g of 12α-hydroxypregna-1,4-diene-3,20-dione (Gas chromatographic analysis revealed that purity thereof was 90%). It has the following physical properties.

Workup

  1. concentrationThe reaction mixturewas concentrated to about one tenth the original volume
  2. distillationby distilling off the methanol under reduced pressure
  3. customTo the concentrated reaction mixture
  4. washthe solution was washed in sequence with water, diluted hydrochloric acid and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationwere distilled off under reduced pressure
  7. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-20ea0db117154ea4bff9a972fce3c7ab
Source dataset
uspto-grants-1989_09
Patent number
US04867914

Reaction notes

Loading…