Hydrochloric Acid → CHOL-5-EN-24-oic acid, 3-hydroxy-, methyl ester, (3beta)-

HRID 2052411Notes

Reaction equation

HRID 2052411 reaction equation
[CH3:1][O:2][C:3](=[O:31])[CH2:4][CH2:5][C@H:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15]([CH2:16][C@@H:17]([O:27]C(=O)C)[CH2:18][CH2:19]2)=[CH:14][CH2:13]3)[CH2:10][CH2:9]1)[CH3:7].[OH-].[K+].Cl>CO>[CH3:1][O:2][C:3](=[O:31])[CH2:4][CH2:5][C@H:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15]([CH2:16][C@@H:17]([OH:27])[CH2:18][CH2:19]2)=[CH:14][CH2:13]3)[CH2:10][CH2:9]1)[CH3:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 10928144HCID 10928144, compound

Product 1

HCID 11153463CHOL-5-EN-24-oic acid, 3-hydroxy-, methyl ester, (3beta)-Yield 37.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

60.1 g of the crude 3β-acetoxy-5-cholenic acid methyl ester was refluxed with a solution of 56.0 g of potassium hydroxide in 1.35 liters of methanol for two hours. The solution was cooled to room temperature and poured into 500 ml of 10% hydrochloric acid. The precipitate was isolated by filtration, washed with water and dried. The crude 3β-hydroxy-5-cholenic acid weighed 50.1 g. Of this, 20.3 g was refluxed for 22 hours with 2 liters of methanol containing 1 g of p-toluenesulfonic acid. The solvent was removed by distillation, the residue dissolved in ether, washed with dilute alkali and water, and the solvent evaporated. 20.3 g of 3β-hydroxy-5-cholenic acid methyl ester was obtained. On recrystallization from heptane the mp was 144°-145° C. Anal. Calcd for C25H40O3 : C, 77.27; H, 10.38. Found: C, 77.04; H, 10.01.

Workup

  1. customThe precipitate was isolated by filtration
  2. washwashed with water
  3. customdried
  4. temperatureOf this, 20.3 g was refluxed for 22 hours with 2 liters of methanol containing 1 g of p-toluenesulfonic acid
  5. customThe solvent was removed by distillation
  6. dissolutionthe residue dissolved in ether
  7. washwashed with dilute alkali and water
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-4a4c5fe326a145599d8f10d71352c11e
Source dataset
uspto-grants-1980_01
Patent number
US04183852

Reaction notes

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