Sodium Hydroxide → 7-[3,4-Dihydroxy-2-(3-hydroxyoctyl)cyclopentyl]heptanoic acid

HRID 1580788Notes

Reaction equation

HRID 1580788 reaction equation
[OH:1][CH:2]1[CH:6]([OH:7])[CH2:5][CH:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16]CC)=[O:15])[CH:3]1[CH2:19][CH2:20][CH:21]([OH:27])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].[OH-].[Na+]>C(O)C>[OH:1][CH:2]1[CH:6]([OH:7])[CH2:5][CH:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH:3]1[CH2:19][CH2:20][CH:21]([OH:27])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20354857Ethyl 7-[3,4-dihydroxy-2-(3-hydroxyoctyl)cyclopentyl]heptanoate

Product 1

HCID 203548487-[3,4-Dihydroxy-2-(3-hydroxyoctyl)cyclopentyl]heptanoic acidYield 45.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 7-[3,4-dihydroxy-2-(3-hydroxyoctyl)cyclopentyl]heptanoate (2.6 g.) [prepared as described in (p) above], ethanol (50 ml.) and 2N aqueous sodium hydroxide solution (50 ml.) were heated together at reflux for 18 hours. The ethanol was removed in vacuo, water (25 ml.) was added and the mixture was washed with diethyl ether. The aqueous phase { which has a solution of sodium 7-[3,4-dihydroxy-2-(3-hydroxyoctyl)cyclopentyl]heptanoate} was acidified to pH 1 by the dropwise addition of concentrated hydrochloric acid, extracted with diethyl ether, and the ethereal extract dried over magnesium sulphate and evaporated in vacuo to give 7-[3,4-dihydroxy-2-(3-hydroxyoctyl)cyclopentyl]heptanoic acid (1.1 g.).

Workup

  1. temperatureat reflux for 18 hours
  2. customThe ethanol was removed in vacuo, water (25 ml.)
  3. additionwas added
  4. washthe mixture was washed with diethyl ether
  5. additionwas acidified to pH 1 by the dropwise addition of concentrated hydrochloric acid
  6. extractionextracted with diethyl ether
  7. extractionthe ethereal extract
  8. dry with materialdried over magnesium sulphate
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-5bdcefae24d04e6a8d46ce443f55993e
Source dataset
uspto-grants-1976_01
Patent number
US03933890

Reaction notes

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