Sodium Hydroxide → HCID 21454182, compound

HRID 436327Notes

Reaction equation

HRID 436327 reaction equation
[CH2:1]([C:5]1[CH2:10][CH2:9][C:8]([CH:16]([CH3:22])[C:17]([O:19]CC)=[O:18])([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:7](=[O:23])[CH:6]=1)[CH:2]([CH3:4])[CH3:3].C(C1CCC(C(C)C(OCC)=O)C(=O)C=1)C(C)C.[OH-].[Na+].C(C1CCC(C(C)C(O)=O)(C(O)=O)C(=O)C=1)C(C)C.C(C1CCC(C(C)C(O)=O)C(=O)C=1)C(C)C>C(O)C>[C:11]([C:8]1([CH:16]([CH3:22])[C:17]([OH:19])=[O:18])[CH2:9][CH2:10][C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[CH:6][C:7]1=[O:23])([O:13][CH2:14][CH3:15])=[O:12]

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 20347224HCID 20347224, compoundHCID 20347225HCID 20347225, compoundHCID 21454187HCID 21454187, compoundHCID 21454190HCID 21454190, compound

Product 1

HCID 21454182HCID 21454182, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

A chromatographed 1 gm. mixture of ethyl 2-(4-isobutyl-1-carboethoxy-2-oxocyclohex-3-enyl)propionate and ethyl 2-(4-isobutyl-2-oxocyclohex-3-enyl)propionate was dissolved in ethanol (4.0 ml.) and then 5.5 ml. of 1 N sodium hydroxide solution was added. The resulting mixture was stirred at 40° C. for 20 hours and then concentrated to about 7 ml. volume. The aqueous residue was extracted with 5 ml. of Skellysolve B and the extract was backwashed with 3 ml. of 1 N sodium hydroxide. The aqueous phases were combined and acidified, extracted as before, dried and concentrated to give an oil, 0.672 g. This oil product consisted of 2-(4-isobutyl-1-carboxy-2-oxocyclohex-3-enyl)propionic acid and 2-(4-isobutyl-2-oxo-cyclohex-3-enyl)propionic acid. This was shown by taking gas liquid chromatographs (glc.) and mass spectra of portions of the product oil which had been converted to silyl esters and methyl esters.

Workup

  1. concentrationconcentrated to about 7 ml
  2. extractionThe aqueous residue was extracted with 5 ml
  3. extractionextracted as before,
  4. customdried
  5. concentrationconcentrated
  6. customto give an oil, 0.672 g

Sources & evidence

ORD record
ord-d537b2f74a4644be98d7e147a0448934
Source dataset
uspto-grants-1977_02
Patent number
US04008270

Reaction notes

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