Acetone → 6-Acetoxy-2-hydroxy-2,5,7,8-tetramethylchroman

HRID 2399045Notes

Reaction equation

HRID 2399045 reaction equation
[C:1]([O:4][C:5]1[C:6]([CH3:20])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([O:18]C)([CH3:17])[CH2:9][CH2:8]2)(=[O:3])[CH3:2].CC(C)=O.Cl>O>[C:1]([O:4][C:5]1[C:6]([CH3:20])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([OH:18])([CH3:17])[CH2:9][CH2:8]2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 144156636-Acetoxy-2-methoxy-2,5,7,8-tetramethylchroman

Product 1

HCID 144156666-Acetoxy-2-hydroxy-2,5,7,8-tetramethylchroman

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (± )-6-acetoxy-2-methoxy-2,5,7,8-tetramethylchroman in 2500 ml. of acetone was added 2000 ml. of H2O followed by 16.6 ml. of concentrated aqueous HCl. Solvent was distilled from the stirred mixture until the head temperature reached 90 degrees centrigrade. The suspension was cooled in an H2O bath to 50 degrees centigrade. At 70 degrees centigrade, 2000 ml. of acetone was added, giving a clear solution. The solution was seeded occasionally until crystallization began. After 3.5 hours, 1500 ml. of H2O was added and the suspension was cooled in an ice bath. The solid was removed by filtration, washed with H2O and dried at 50 degrees centigrade/0.1 mmHg. to give (± )-6-acetoxy-2-hydroxy-2,5,7,8-tetramethylchroman as a granular yellow-tan solid, sintering from 114 degrees centigrade, m.p. 127°-132 degrees centigrade.

Workup

  1. distillationSolvent was distilled from the stirred mixture until the head temperature
  2. customreached 90 degrees
  3. temperatureThe suspension was cooled in an H2O bath to 50 degrees centigrade
  4. customAt 70 degrees centigrade
  5. additionof acetone was added
  6. customgiving a clear solution
  7. customThe solution was seeded occasionally until crystallization
  8. additionof H2O was added
  9. temperaturethe suspension was cooled in an ice bath
  10. customThe solid was removed by filtration
  11. washwashed with H2O
  12. customdried at 50 degrees centigrade/0.1 mmHg

Sources & evidence

ORD record
ord-d45dc97cb23546d6b04f773d4ff02761
Source dataset
uspto-grants-1977_05
Patent number
US04026907

Reaction notes

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