Hydrochloric Acid → 6-Acetoxy-2-hydroxy-2,5,7,8-tetramethylchroman

HRID 328839Notes

Reaction equation

HRID 328839 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].Cl>CC(C)=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

4

Reactant 2

HCID 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 180AcetoneSolvent

Procedure

To a solution of (±)-6-acetoxy-2-methoxy-2,5,7,8-tetramethylchroman in 2500 ml. of acetone was added 2000 ml. of H 2 O followed by 16.6 ml. of concentrated aqueous HCl. Solvent was distilled from the stirred mixture until the head temperature reached 90° centigrade. The suspension was cooled in an H 2 O bath to 50° centigrade. At 70° 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 H 2 O was added and the suspension was cooled in an ice bath. The solid was removed by filtration, washed with H 2 O and dried at 50° centigrade/0.1mmHg. 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° centigrade.

Workup

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

Sources & evidence

ORD record
ord-6c2522f3e18d4b66931378ceb4394978
Source dataset
uspto-grants-1977_04
Patent number
US04018799

Reaction notes

Loading…