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

HRID 328517Notes

Reaction equation

HRID 328517 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-9ebb6a31ce6a40ac9a9f96b76124f56f
Source dataset
uspto-grants-1977_04
Patent number
US04017534

Reaction notes

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