Benzoic Acid → HCID 70467390, compound

HRID 64722Notes

Reaction equation

HRID 64722 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].O.[CH2:13]([C@H:15]1[CH2:20][C@H:19]2[C@H:21]3[C@H:30]([CH2:31][CH2:32][C@:17]2([CH3:18])[C@H:16]1[O:34][C:35](=[O:38])[CH2:36]Br)[C@@H:29]1[C:24](=[CH:25][C:26](=[O:33])[CH2:27][CH2:28]1)[CH2:23][CH2:22]3)[CH3:14]>CC(C)=O>[CH2:13]([C@H:15]1[CH2:20][C@H:19]2[C@H:21]3[C@H:30]([CH2:31][CH2:32][C@:17]2([CH3:18])[C@H:16]1[O:34][C:35](=[O:38])[CH2:36][O:8][C:1](=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C@@H:29]1[C:24](=[CH:25][C:26](=[O:33])[CH2:27][CH2:28]1)[CH2:23][CH2:22]3)[CH3:14]

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 1559376416beta-Ethyl-17beta-bromoacetoxy-4-estren-3-one

Product 1

HCID 70467390HCID 70467390, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 30 ml of acetone is dissolved 0.49 g of benzoic acid, and 2 ml of 2 N-NaOH and 5 ml of water are added, followed by addition of 0.88 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one. The mixture is refluxed for 3 hours. After cooling, the solvent is distilled off under reduced pressure and the residue is extracted with 100 ml of ethyl acetate. The organic layer is separated, washed with water and saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent is then distilled off under reduced pressure and the residue is chromatographed on a silica gel column. After passage of 350 ml of diisopropyl ether, the solvent is distilled off under reduced pressure. To the residue is added a small amount of diisopropyl ether, followed by filtration to give 0.86 g of the above-identified compound as a white powder.

Workup

  1. additionare added
  2. temperatureThe mixture is refluxed for 3 hours
  3. temperatureAfter cooling
  4. distillationthe solvent is distilled off under reduced pressure
  5. extractionthe residue is extracted with 100 ml of ethyl acetate
  6. customThe organic layer is separated
  7. washwashed with water and saturated aqueous sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe solvent is then distilled off under reduced pressure
  10. customthe residue is chromatographed on a silica gel column
  11. distillationAfter passage of 350 ml of diisopropyl ether, the solvent is distilled off under reduced pressure
  12. additionTo the residue is added a small amount of diisopropyl ether
  13. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-a175a5b1bb7a40e594dc1118431ce9c5
Source dataset
uspto-grants-1986_09
Patent number
US04609650

Reaction notes

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