Water → HCID 12893752, compound

HRID 1613002Notes

Reaction equation

HRID 1613002 reaction equation
[OH2:1].[OH-].[Na+].[OH:4][C:5]1[CH2:9][CH2:8][C:7](=O)[C:6]=1[CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18]>C(O)(=O)C>[OH:1][CH:8]1[CH2:9][C:5](=[O:4])[C:6]([CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:7]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 67790267HCID 67790267, compound

Product 1

HCID 12893752HCID 12893752, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To the compound [VIII-2] (2.50 g) obtained above are added water (123.8 g) and acetic acid (0.19 g), and the pH value of the mixture is adjusted to pH 4.2 with 5% aqueous sodium hydroxide solution and the mixture is heated with stirring at 100° C. for 26 hours. After completion of the reaction, the reaction mixture is cooled and extracted twice with methyl isobutyl ketone (50 ml). The organic layer is separated and concentrated to give a mixture (1.78 g, yield; 71%) of 4-hydroxy-2-(6-methoxycarbonyl-cis-3-hexenyl)-2-cyclopentenone (racemic 4-hydroxycyclopentenone) and 3-hydroxy-2-(6-methoxycarbonyl-cis-3-hexenyl)-2-cyclopentenone [IX-2] (ratio thereof=4.9:5.1).

Workup

  1. customTo the compound [VIII-2] (2.50 g) obtained
  2. temperaturethe mixture is heated
  3. customAfter completion of the reaction
  4. temperaturethe reaction mixture is cooled
  5. extractionextracted twice with methyl isobutyl ketone (50 ml)
  6. customThe organic layer is separated
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8a8191b4c8234ca6af5e864576dc0eea
Source dataset
uspto-grants-1993_03
Patent number
US05191109

Reaction notes

Loading…