Tetrahydrofuran → 2-(1,3,5-Triethylphenyl)-2-oxoacetic acid

HRID 579245Notes

Reaction equation

HRID 579245 reaction equation
O1CCCC1.[CH2:6]([C:8]1([C:18](=[O:24])[C:19]([O:21]CC)=[O:20])[CH:13]=[C:12]([CH2:14][CH3:15])[CH:11]=[C:10]([CH2:16][CH3:17])[CH2:9]1)[CH3:7].[OH-].[Na+]>O>[CH2:6]([C:8]1([C:18](=[O:24])[C:19]([OH:21])=[O:20])[CH:9]=[C:10]([CH2:16][CH3:17])[CH:11]=[C:12]([CH2:14][CH3:15])[CH2:13]1)[CH3:7]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66691385Ethyl 2-(1,3,5-triethylphenyl)-2-oxoacetate

Product 1

HCID 666915612-(1,3,5-Triethylphenyl)-2-oxoacetic acidYield 92.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 3 L volume four-necked flask, tetrahydrofuran (750 ml) and ethyl 2-(1,3,5-triethylphenyl)-2-oxoacetate (9-b) (261.0 g) were added, and sodium hydroxide (88 g) dissolved in water (237 g) was added dropwise thereto at about 15-20° C. The resulting mixture was stirred at room temperature for 1 hour and 30 minutes. The solid was removed by decantation. The liquid part was concentrated under reduced pressure. The residue was extracted with toluene and water. After the organic layer was removed, the aqueous layer was washed with toluene. The pH of the aqueous layer was adjusted to 1 with dilute sulfuric acid under cooling, and then the aqueous layer was extracted with toluene. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and filtered to remove the insolubles. The filtrate was concentrated under reduced pressure to give 214.8 g of 2-(1,3,5-triethylphenyl)-2-oxoacetic acid (8-b).

Workup

  1. additionwas added dropwise
  2. customat about 15-20° C
  3. customThe solid was removed by decantation
  4. concentrationThe liquid part was concentrated under reduced pressure
  5. extractionThe residue was extracted with toluene and water
  6. customAfter the organic layer was removed
  7. washthe aqueous layer was washed with toluene
  8. temperatureunder cooling
  9. extractionthe aqueous layer was extracted with toluene
  10. washThe organic layer was washed with water
  11. dry with materialdried over anhydrous magnesium sulfate
  12. filtrationfiltered
  13. customto remove the insolubles
  14. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3719a0bdef014c9ebd265148913bd5e4
Source dataset
uspto-grants-2015_05
Patent number
US09040709B2

Reaction notes

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