Sulfuric Acid → 4,6-Dimethyl-7-hydroxy-2-phenyl-1-indanone

HRID 330235Notes

Reaction equation

HRID 330235 reaction equation
S(=O)(=O)(O)O.[CH3:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[C:9]([C:14](=[O:23])[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH2:16])[C:8]=1[OH:24]>>[CH3:13][C:11]1[CH:12]=[C:7]([CH3:6])[C:8]([OH:24])=[C:9]2[C:10]=1[CH2:16][CH:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:14]2=[O:23]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 148734432,4-Dimethyl-6-(2-phenylacryloyl)phenol

Product 1

HCID 140302654,6-Dimethyl-7-hydroxy-2-phenyl-1-indanoneYield 70.3%

Procedure

Into 15 mI of concentrated sulfuric acid, under ice-cooled condition with stirring, 3.0 g of 2,4-dimethyl-6-(2-phenylacryloyl)phenol was added gradually, then the whole mixture was stirred at room temperature for 1 hour. The reaction mixture was poured in 100 g of ice and extracted with 200 ml of methylene chloride. The extract was washed with water and dried with anhydrous magnesium sulfate, then was concentrated under a reduced pressure to obtain the residue. The residue was recrystallized from ethanol to obtain 2.11 g of 2,3-dihydro-4,6-dimethyl-2-phenyl-7-hydroxy-1H-inden-1-one.

Workup

  1. stirringthe whole mixture was stirred at room temperature for 1 hour
  2. extractionextracted with 200 ml of methylene chloride
  3. washThe extract was washed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationwas concentrated under a reduced pressure
  6. customto obtain the residue
  7. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-7f5591cd246c42f3b1a7d1dcbf6dbfce
Source dataset
uspto-grants-1990_01
Patent number
US04895847

Reaction notes

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