Hydrochloric Acid → HCID 54455690, compound

HRID 1076963Notes

Reaction equation

HRID 1076963 reaction equation
[C:1]([CH2:5][C:6]1(C(OC)=O)[C@@H:10]([CH:11]=[CH:12][CH:13]([OH:19])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:9][C@H:8](C(OC)=O)[C:7]1=[O:24])([O:3]C)=[O:2].[OH-].[Na+].Cl>O.CO>[OH:19][CH:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:12]=[CH:11][C@@H:10]1[CH2:9][CH2:8][C:7](=[O:24])[C@H:6]1[CH2:5][C:1]([OH:3])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70601232HCID 70601232, compound

Product 1

HCID 54455690HCID 54455690, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A suspension of dimethyl trans-1-(carbomethoxymethyl)-5-(3-hydroxy-1-octenyl)-2-oxo-1,3-cyclopentanedicarboxylate (26.24 g), described in Example 42, in a solution of sodium hydroxide (12 g) in 70 ml of water and 80 ml of methanol is heated at reflux for 2 hr. The reaction mixture is cooled, acidified to pH 6 with 2N HCl. The resulting oil is extracted with ether. The ether extract is washed with water, dried (MgSO4) and the solvent removed. The residue is subjected to chromatography on silica gel (850 g). Elution with methanol-chloroform (1:9) yields the title compound, νmaxfilm 3350, 1727 cm-1. The corresponding methyl ester of the title compound, prepared by treatment with diazomethane, has νmaxfilm 3412, 1737 cm-1.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 2 hr
  3. temperatureThe reaction mixture is cooled
  4. extractionThe resulting oil is extracted with ether
  5. extractionThe ether extract
  6. washis washed with water
  7. dry with materialdried (MgSO4)
  8. customthe solvent removed
  9. washElution with methanol-chloroform (1:9)

Sources & evidence

ORD record
ord-5c40d387413b43ef8d7ae1060ec1414b
Source dataset
uspto-grants-1976_05
Patent number
US03959263

Reaction notes

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