Sulfuric Acid → 2,3-Dihydro-1,1,3-trimethyl-3-phenyl-1H-indene

HRID 1576740Notes

Reaction equation

HRID 1576740 reaction equation
S(=O)(=O)(O)O.[CH3:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[CH2:8]>>[CH3:8][C:7]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:7]([CH3:6])([CH3:6])[CH2:8]1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 7407Alpha-Methylstyrene

Product 1

HCID 197932,3-Dihydro-1,1,3-trimethyl-3-phenyl-1H-indeneYield 75%

Conditions

Temperature
145 °C

Procedure

To 6.0 kg. of 62% sulfuric acid at 50°C was added 1.0 kg. of α-methyl styrene over a 5 minute period. The mixture was refluxed (145°C) for 20 hours. After cooling, the lower acid phase was drawn off and discarded. The organic phase was washed with sulfuric acid several times and then with water several times. The product was recrystallized from methanol which afforded 750 g of white crystals with a melting point of 50.5°-52.0°C. The yield was 75%.

Workup

  1. temperatureAfter cooling
  2. washThe organic phase was washed with sulfuric acid several times
  3. customThe product was recrystallized from methanol which

Sources & evidence

ORD record
ord-befa7772906643518004dcb9d98f7633
Source dataset
uspto-grants-1976_09
Patent number
US03983092

Reaction notes

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