Benzene → HCID 53997316, compound

HRID 1607827Notes

Reaction equation

HRID 1607827 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 temperaature for 10 hours. The reaction mixture was 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 driedover anhydrous magnesium sulfate. Low-boiling fractions were distilled off under reduced pressure and the residue was recrystallized from ethyl acetate to give 5.4 g of 12α-hydroxypregna-1,4-diene-3,20-dione (Gaschromatographic analysis revealed that purity thereof was 90%). It has the following physical properties.

Workup

  1. concentrationThe reaction mixture was 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. distillationwere distilled off under reduced pressure
  6. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-006a6b92fe184ab4b508b25d5bae756b
Source dataset
uspto-grants-1989_09
Patent number
US04867913

Reaction notes

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