Hydrochloric Acid → 9-Oxoprostanoic acid

HRID 328836Notes

Reaction equation

HRID 328836 reaction equation
[O:1]=[C:2]1[CH2:17][CH2:16][C@H:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C@H:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12]CC)=[O:11].[OH-].[K+].Cl>CO>[O:1]=[C:2]1[CH2:17][CH2:16][C@H:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C@H:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 22797031HCID 22797031, compound

Product 1

HCID 64547989-Oxoprostanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 300 mg. of ethyl 9-oxoprostanoate in 20 ml. of aqueous methanol (1:1) containing 300 mg. of potassium hydroxide is stirred at 50° C. for 1 hour and then at room temperature for 18 hours. The resulting solution is acidified with 1N hydrochloric acid, concentrated and extracted several times with diethyl ether. The combined ether extracts are washed with saturated sodium chloride solution, dried with anhydrous magnesium sulfate and taken to dryness to give 256 mg. (94%) of product as an oil; λmax 5.75, 5.85 μ; nmr 1H broad singlet δ 9.89 (carboxyl proton, exchangeable).

Workup

  1. additionA suspension of 300 mg
  2. concentrationconcentrated
  3. extractionextracted several times with diethyl ether
  4. washThe combined ether extracts are washed with saturated sodium chloride solution
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customto give 256 mg

Sources & evidence

ORD record
ord-0f00f345f8634da3822c61d1e441d150
Source dataset
uspto-grants-1977_04
Patent number
US04018811

Reaction notes

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