Hydrochloric Acid → AY 22093

HRID 328512Notes

Reaction equation

HRID 328512 reaction equation
[OH:1][CH:2]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:3][CH2:4][C@@H:5]1[C@@H:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18]CC)=[O:17])[C:8](=[O:21])[CH2:7][CH2:6]1.[OH-].[K+].Cl.[Cl-].[Na+]>CO>[OH:1][CH:2]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:3][CH2:4][C@@H:5]1[C@@H:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[C:8](=[O:21])[CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 14797Potassium HydroxideHCID 1859466215-Hydroxy-9-oxoprostanoic acid, ethyl ester

Product 1

HCID 193037AY 22093

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 15 g. of 15-hydroxy-9-oxoprostanoic acid, ethyl ester (Example 50) in 230 ml. of aqueous methanol (1:1) containing 6.45 g. 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, saturated with sodium chloride, and extracted several times wth diethyl ether. The combined ether extracts are washed twice with saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and taken to dryness to give 13.1 g. (94%) of products as an oil. There is essentially no uv absorption; [αD25 0° (1.0% in CHCl3); λmaxKBr 2.80-3.70 (broad), 5.75, 5.87 μ; nmr 2H singlet δ6.65 (hydroxyl and carboxyl protons), 1H broad singlet 3.63 (carbinolic proton), and 3H distorted triplet 0.93 (terminal methyl); mass spectrum: m/e 340.

Workup

  1. additionA suspension of 15 g
  2. extractionextracted several times wth diethyl ether
  3. washThe combined ether extracts are washed twice with saturated sodium chloride solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customto give 13.1 g
  6. customno uv absorption

Sources & evidence

ORD record
ord-039253bf218a4fb585d2520a58f5b4c6
Source dataset
uspto-grants-1977_04
Patent number
US04017534

Reaction notes

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