P-Cresol → 7-hydroxy-3,4-dimethylindan-1-one

HRID 267889Notes

Reaction equation

HRID 267889 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([CH3:8])[CH:2]=1.[C:9]1(=O)[O:13][CH2:12][CH2:11][CH2:10]1.[Cl-].[Al+3].[Cl-].[Cl-].[Cl-].[Na+]>C1C=CC=CC=1>[CH3:9][CH:10]1[C:2]2[C:1](=[C:6]([OH:7])[CH:5]=[CH:4][C:3]=2[CH3:8])[C:12](=[O:13])[CH2:11]1

Participants

6

Reactant 4

HCID 2879P-CresolHCID 5234Sodium ChlorideHCID 7302Gamma-ButyrolactoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 111480357-hydroxy-3,4-dimethylindan-1-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Likewise, a mixture of 21.6 g. (0.2 mol) of p-cresol and 17.2 g. (0.2 mol) of γ-butyrolactone is added into a mixture of 79.8 g. (0.6 mol) of anhydrous aluminium chloride and 15.0 g. (0.26 mol) of sodium chloride which mixture has been molten at 140°C, and the resultant mixture is heated at a temperature of 140°-200°C for about 3 minutes. After cooling, the reaction mixture is poured into a hydrochloric acid-ice and the resulting acidic solution is stirred with benzene. The benzene layer is taken up and dried with anhydrous sodium sulfate. The solvent is removed by distillation, and the residue is further subjected to vacuum distillation, whereby yellowish liquid is distilled out at 95°-105°C/2mmHg, which liquid is solidified on cooling. Upon recrystallization from n-hexane after decolorization with active carbon, 14.9 g. of whitish-purple crystals of 3,4-dimethyl-7-hydroxyindan-1-one having a melting point of 52°-53°C is obtained.

Workup

  1. additionLikewise, a mixture of 21.6 g
  2. customhas been molten at 140°C
  3. temperatureAfter cooling
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe solvent is removed by distillation
  6. distillationthe residue is further subjected to vacuum distillation, whereby yellowish liquid
  7. distillationis distilled out at 95°-105°C/2mmHg, which liquid
  8. temperatureon cooling
  9. customUpon recrystallization from n-hexane after decolorization with active carbon, 14.9 g

Sources & evidence

ORD record
ord-39b2570fd7144f6f9d0239e720f79172
Source dataset
uspto-grants-1976_03
Patent number
US03944679

Reaction notes

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