Sodium Hydroxide → HCID 15229875, compound

HRID 1779495Notes

Reaction equation

HRID 1779495 reaction equation
C([O:4][C:5]1[C:28]([CH3:29])=[CH:27][C:8]([O:9][CH2:10][CH2:11][C:12]2[CH:26]=[CH:25][C:15]([O:16][C:17]([CH3:24])([CH3:23])[C:18]([O:20]CC)=[O:19])=[CH:14][CH:13]=2)=[C:7]([CH3:30])[C:6]=1[CH3:31])(=O)C.[OH-].[Na+]>C(O)C>[OH:4][C:5]1[C:28]([CH3:29])=[CH:27][C:8]([O:9][CH2:10][CH2:11][C:12]2[CH:26]=[CH:25][C:15]([O:16][C:17]([CH3:24])([CH3:23])[C:18]([OH:20])=[O:19])=[CH:14][CH:13]=2)=[C:7]([CH3:30])[C:6]=1[CH3:31]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15229882HCID 15229882, compound

Product 1

HCID 15229875HCID 15229875, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10.5 g (0.0245 mol) of the ethyl 2-{4-[2-(4-acetoxy-2,3,5-trimethylphenoxy)ethyl]phenoxy}isobutyrate so obtained are introduced with 500 ml of ethanol and 50 ml of 1N sodium hydroxide solution into a three-necked flask that is equipped with a stirrer and a condenser and is placed under a nitrogen atmosphere. The whole is heated under reflux for 3 hours and then concentrated to dryness. The residue is taken up in water and extracted several times with ether. The aqueous phase is acidified with 55 cm3 of 1N hydrochloric acid and then extracted several times with ether. The combined ethereal phases are washed with water, dried over sodium sulphate and concentrated to dryness. The residue is chromatographed on 1.4 liters of Amicon silica (0.035-0.070 mm) while eluting with a mixture of methylene chloride and ethyl acetate (70:30). The desired fractions are concentrated to dryness. The residue is dissolved in 20 ml of ether. The whole is diluted with petroleum ether and cooled. Crystallisation is observed. The crystals are filtered off with suction and dried at 45° C. under 133 Pa to yield 6 g of 2-{4-[2-(4-hydroxy-2,3,5-trimethylphenoxy)ethyl]phenoxy}isobutyric acid in the form of white crystals melting (K) at 69° C. Yield: 68%.

Workup

  1. customis equipped with a stirrer and a condenser
  2. temperatureThe whole is heated
  3. temperatureunder reflux for 3 hours
  4. concentrationconcentrated to dryness
  5. extractionextracted several times with ether
  6. extractionextracted several times with ether
  7. washThe combined ethereal phases are washed with water
  8. dry with materialdried over sodium sulphate
  9. concentrationconcentrated to dryness
  10. customThe residue is chromatographed on 1.4 liters of Amicon silica (0.035-0.070 mm)
  11. washwhile eluting with a mixture of methylene chloride and ethyl acetate (70:30)
  12. concentrationThe desired fractions are concentrated to dryness
  13. dissolutionThe residue is dissolved in 20 ml of ether
  14. additionThe whole is diluted with petroleum ether
  15. temperaturecooled
  16. customCrystallisation
  17. filtrationThe crystals are filtered off with suction
  18. customdried at 45° C. under 133 Pa

Sources & evidence

ORD record
ord-c98e127012a64295befa623e3bd539fd
Source dataset
uspto-grants-1997_05
Patent number
US05627205

Reaction notes

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