Acetone → 2H-1-Benzopyran-2,6-diol, 3,4-dihydro-2,5,7,8-tetramethyl-

HRID 328855

Reaction equation

HRID 328855 reaction equation
[OH:1][C:2]1[C:3]([CH3:17])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([O:15]C)([CH3:14])[CH2:6][CH2:5]2.CC1C(O)=C(C)C(C)=C(C=1)O.CC(C)=O.Cl>O>[OH:15][C:7]1([CH3:14])[CH2:6][CH2:5][C:4]2[C:9](=[C:10]([CH3:13])[C:11]([CH3:12])=[C:2]([OH:1])[C:3]=2[CH3:17])[O:8]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 12785TrimethylhydroquinoneHCID 1037632H-1-Benzopyran-6-ol, 3,4-dihydro-2-methoxy-2,5,7,8-tetramethyl-

Product 1

HCID 1037372H-1-Benzopyran-2,6-diol, 3,4-dihydro-2,5,7,8-tetramethyl-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of (±)-6-hydroxy-2-methoxy-2,5,7,8-tetramethylchroman, prepared as described in Example 1 from 1.0 mole of trimethylhydroquinone, in 1250 ml. of acetone, 1000 ml. of H2O and 8.30 ml. of conc. HCl was heated at reflux under N2. The solvent was removed by distillation until the distilling head temperature reached 95°. The suspension was cooled to 70°, diluted with 800 ml. of acetone, cooled to ca. 15° and stripped of solvent at reduced pressure and 30° to ca. 1000 ml. The resulting suspension was cooled, filtered and dried to give (±)-2,6-dihydroxy-2,5,7,8-tetramethylchroman as a grey-tan powder, m.p. 105°-107°.

Workup

  1. temperatureat reflux under N2
  2. customThe solvent was removed by distillation until the distilling head temperature
  3. customreached 95°
  4. temperatureThe suspension was cooled to 70°
  5. additiondiluted with 800 ml
  6. temperatureof acetone, cooled to ca. 15°
  7. temperatureThe resulting suspension was cooled
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-965226737cd048c796b6ab77ecae8c92
Source dataset
uspto-grants-1977_04
Patent number
US04018799

Linked notes

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