Sodium Hydroxide → 6-Hydroxy-2,5,7,8-tetramethylchroman-2-acetic acid

HRID 263927Notes

Reaction equation

HRID 263927 reaction equation
C([O:4][C:5]1[C:6]([CH3:24])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([CH3:23])([CH2:17][C:18]([O:20]CC)=[O:19])[CH2:9][CH2:8]2)(=O)C.[OH-].[Na+]>C(O)C.O>[OH:4][C:5]1[C:6]([CH3:24])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([CH3:23])([CH2:17][C:18]([OH:20])=[O:19])[CH2:9][CH2:8]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 54216525Ethyl 6-acetoxy-2,5,7,8-tetramethylchroman-2-acetate

Product 1

HCID 55926-Hydroxy-2,5,7,8-tetramethylchroman-2-acetic acidYield 70.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of ethyl 6-acetoxy-2,5,7,8-tetramethylchroman-2-acetate (36.5 g, ~108 mmol) and 50% aqueous sodium hydroxide (110 mL) in a mixture of ethanol (500 mL) and water (500 mL) was stirred at ambient temperature for 7 h. The reaction mixture was extracted with hexane (2×200 mL). The pH of the resulting solution was adjusted to ~2 with concentrated hydrochloric acid. Water (~200 mL) was added and the reaction mixture was cooled in an ice/water bath. Crystallization was induced by scratching with a glass rod and the solid that formed was collected by filtration. The solid was recrystallized from an ethanol/water mixture to give 20.2 g (70.9% yield) of the desired product as a tan solid.

Workup

  1. extractionThe reaction mixture was extracted with hexane (2×200 mL)
  2. additionWater (~200 mL) was added
  3. temperaturethe reaction mixture was cooled in an ice/water bath
  4. customCrystallization
  5. customthe solid that formed
  6. filtrationwas collected by filtration
  7. customThe solid was recrystallized from an ethanol/water mixture

Sources & evidence

ORD record
ord-4cfec0fb56c847b1913469c13174c2f5
Source dataset
uspto-grants-1997_07
Patent number
US05646149

Reaction notes

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