Potassium Hydroxide → 9-Ethylenedioxy-15-hydroxy-15-methyl-prostanoic acid

HRID 1580212Notes

Reaction equation

HRID 1580212 reaction equation
[CH2:1]1[CH2:20][O:19][CH:18]2[CH:3]([C@@H:4]([C@@H:16]([CH2:21][CH2:22][C:23]([OH:30])([CH3:29])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:17]2)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13]CC)=[O:12])[O:2]1.[OH-].[K+].OP([O-])(O)=O.[Na+]>CO.O>[CH2:1]1[CH2:20][O:19][CH:18]2[CH:3]([C@@H:4]([C@@H:16]([CH2:21][CH2:22][C:23]([OH:30])([CH3:29])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:17]2)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])[O:2]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 23672064Monosodium phosphateHCID 68124131Ethyl 9-ethylenedioxy-15-hydroxy-15-methylprostanoate

Product 1

HCID 681237699-Ethylenedioxy-15-hydroxy-15-methyl-prostanoic acid

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of 1.33 g. of ethyl 9-ethylenedioxy-15-hydroxy-15-methyl prostanoate (Example 57) in 20 ml. of methanol-water (1:1) containing 500 mg. of potassium hydroxide is stirred at room temperature for 18 hours. The solution is neutralized with 30% aqueous sodium phosphate monobasic and extracted with ether. The ether extract is washed with saturated sodium chloride solution, dried with anhydrous magnesium sulfate and taken to dryness to give 1.23 g. (99%) of viscous oil; λ max. 2.94-4.00 (broad) (hydroxyl and carboxyl groups) and 5.85 μ (acid carbonyl group).

Workup

  1. extractionextracted with ether
  2. extractionThe ether extract
  3. washis washed with saturated sodium chloride solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customto give 1.23 g

Sources & evidence

ORD record
ord-b50e92f57c3d49f5b56b8f52a4a0e732
Source dataset
uspto-grants-1976_01
Patent number
US03932463

Reaction notes

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