Bisphenol A → 1,1,3,3-Tetramethylindan-5-ol

HRID 442471

Reaction equation

HRID 442471 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].O[C:13]1[CH:18]=CC(C(C2C=CC(O)=CC=2)(C)C)=C[CH:14]=1.B(F)(F)F.CCOCC>C1(C)C=CC=CC=1>[OH:11][C:8]1[CH:7]=[C:6]2[C:5](=[CH:10][CH:9]=1)[C:1]([CH3:4])([CH3:2])[CH2:3][C:13]2([CH3:18])[CH3:14]

Participants

5

Reactant 3

HCID 6623Bisphenol AHCID 73934-tert-ButylphenolHCID 8000Boron trifluoride etherate

Product 1

HCID 1045671,1,3,3-Tetramethylindan-5-olYield 37.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

172 g (1.15 mol) of 4-tert.-butylphenol, 57.5 g (0.25 mol) of 2,2-bis-(4- hydroxyphenyl)-propane and 5 g of boron trifluoride etherate are stirred in an autoclave for 6 hours at around 150° C. The reaction mixture is then diluted with 400 ml of toluene and the catalyst washed out with 900 ml of water used in several portions. The solvent is then distilled off. 17.6 g (0.093 mol) of 5-hydroxy-1,1,3,3-tetramethyl indane were isolated from the 216.7 g reaction product by fractional distillation.

Workup

  1. washthe catalyst washed out with 900 ml of water
  2. distillationThe solvent is then distilled off

Sources & evidence

ORD record
ord-2aba90c874e2498e813948b5fd8cdda5
Source dataset
uspto-grants-1977_08
Patent number
US04045499

Linked notes

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