Acetone → HCID 14210611, compound

HRID 580376Notes

Reaction equation

HRID 580376 reaction equation
C[O:2][C:3]1([CH3:18])[CH2:8][CH2:7][C:6]2[C:9]([CH3:17])=[C:10]([O:15][CH3:16])[C:11]([CH3:14])=[C:12]([CH3:13])[C:5]=2[O:4]1.CC(C)=O.Cl>O>[CH3:16][O:15][C:10]1[C:11]([CH3:14])=[C:12]([CH3:13])[C:5]2[O:4][C:3]([CH3:18])([OH:2])[CH2:8][CH2:7][C:6]=2[C:9]=1[CH3:17]

Participants

5

Reactant 3

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 14210614HCID 14210614, compound

Product 1

HCID 14210611HCID 14210611, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 84.3 g (0.337 mole) of rac.-2,6-dimethoxy-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran, 370 ml of acetone, 300 ml of water, and 2.5 ml of conc. hydrochloric acid was distilled until the distillate temperature reached 90° C. After being cooled, the mixture was diluted with water and extracted three times with ether. The ether extracts were combined, washed with saturated brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was recrystallized from aqueous acetone giving rac.-6-methoxy-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-2-ol as an off-white solid, in crops of 34.6 g (43.5%) and 11.1 g (13.9%).

Workup

  1. distillationwas distilled until the distillate temperature
  2. customreached 90° C
  3. temperatureAfter being cooled
  4. additionthe mixture was diluted with water
  5. extractionextracted three times with ether
  6. washwashed with saturated brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was recrystallized from aqueous acetone

Sources & evidence

ORD record
ord-3f2a66ea34b546eebf538e1655f9c5f3
Source dataset
uspto-grants-1988_06
Patent number
US04752646

Reaction notes

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