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

HRID 442440Notes

Reaction equation

HRID 442440 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 was 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-0527d2991f224c9c96f8085fa011d050
Source dataset
uspto-grants-1977_08
Patent number
US04045467

Reaction notes

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