Toluene → 1,1,3,3-Tetramethylindan-5-ol

HRID 1076112Notes

Reaction equation

HRID 1076112 reaction equation
[CH3:1][C:2](=C)[CH3:3].[CH:5]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)([CH3:7])[CH3:6].[C:15]1(C)C=CC=CC=1>>[CH3:6][C:5]1([CH3:15])[C:8]2[C:9](=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=2)[C:2]([CH3:3])([CH3:1])[CH2:7]1

Participants

4

Reactant 3

HCID 1140TolueneHCID 74654-IsopropylphenolHCID 8255Isobutylene

Product 1

HCID 1045671,1,3,3-Tetramethylindan-5-ol

Conditions

Temperature
150 °C

Procedure

112 g (2 mol) of isobutylene were pumped for 1 hour into 136 g (1 mol) of 4-isopropyl-phenol in 100 ml of toluene and 30 g of an acid activated Fuller's earth in an autoclave with stirring at 150°C. The reaction mixture was then stirred for 6 hours at 150°C. After removal of the catalyst by filtration, 120 g of pure 1,1,3,3-tetramethyl-5-hydroxyindane were obtained by fractional distillation; Bp12 : 144°C; Mp: 119°C. ##SPC11##

Workup

  1. stirringThe reaction mixture was then stirred for 6 hours at 150°C
  2. customAfter removal of the catalyst
  3. filtrationby filtration

Sources & evidence

ORD record
ord-bcc3db0e270c4d8080d663d201e44c22
Source dataset
uspto-grants-1976_05
Patent number
US03954889

Reaction notes

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