Sulfuric Acid → 1,1,3,3-Tetramethylindan-5-ol

HRID 442469Notes

Reaction equation

HRID 442469 reaction equation
OC1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)([CH3:10])[CH3:9])=CC=1.S(=O)(=O)(O)O.[CH3:23]C(=C)C>C1(C)C=CC=CC=1>[OH:17][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[C:8]([CH3:9])([CH3:10])[CH2:5][C:6]2([CH3:7])[CH3:23]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6623Bisphenol AHCID 8255Isobutylene

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

114 g (0.5 mol) of 2,2-bis-(4-hydroxyphenyl)-propane, 6 ml of concentrated sulphuric acid and 90 g (1.6 mol) of isobutylene are stirred in an autoclave for 6 hours at 180° C. After cooling, the reaction product is taken up in 150 ml of toluene and washed with 10 % by weight aqueous sodium hydrogen carbonate solution to remove the catalyst. The toluene solution is then distilled to remove the solvent and the residue of 176.9 g is subsequently subjected to fractional distillation, giving 20.6 g (22 % of the theoretical) of 5-hydroxy-1,1,3,3-tetramethyl indane.

Workup

  1. temperatureAfter cooling
  2. washwashed with 10 % by weight aqueous sodium hydrogen carbonate solution
  3. customto remove the catalyst
  4. distillationThe toluene solution is then distilled
  5. customto remove the solvent
  6. distillationthe residue of 176.9 g is subsequently subjected to fractional distillation

Sources & evidence

ORD record
ord-7fbb91d7013e40d7b8a621ed8ac9db12
Source dataset
uspto-grants-1977_08
Patent number
US04045499

Reaction notes

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