Sodium Hydroxide → Stillingic acid

HRID 1859367Notes

Reaction equation

HRID 1859367 reaction equation
[OH-].[Na+].[C:3]([O:14]CC)(=[O:13])/[CH:4]=[CH:5]/[CH:6]=[CH:7]\[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]>O1CCCC1>[C:3]([OH:14])(=[O:13])/[CH:4]=[CH:5]/[CH:6]=[CH:7]\[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 5281162Ethyl (2E,4Z)-deca-2,4-dienoate

Product 1

HCID 5282781Stillingic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An aqueous solution of sodium hydroxide (10%, 22 ml) was added to a solution of technical grade ethyl (2E,4Z)-2,4-decadienoate (10 g) in tetrahydrofuran (100 ml). The mixture was heated under reflux for 5 hours with rapid stirring in a nitrogen atmosphere. After allowing to cool to room temperature, tetrahydrofuran was removed on a rotary evaporator, the residue was diluted with water (100 ml), and acidified to pH 2 with 6N HCl. The acid was extracted with ether (3×100 ml) and the combined extracts were washed with water (2×50 ml) and brine (50 ml) and dried using anhydrous magnesium sulfate. Removal of ether under reduced pressure gave (2E,4Z)-2,4-decadienoic acid. This product was used in the next step without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. customtetrahydrofuran was removed on a rotary evaporator
  4. additionthe residue was diluted with water (100 ml)
  5. extractionThe acid was extracted with ether (3×100 ml)
  6. washthe combined extracts were washed with water (2×50 ml) and brine (50 ml)
  7. customdried
  8. customRemoval of ether under reduced pressure

Sources & evidence

ORD record
ord-1cd46888ab694992a0c359bb9e3288b9
Source dataset
uspto-grants-2003_03
Patent number
US06528049B2

Reaction notes

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