Isobutylene → 6-Chloro-1,1,3,3-tetramethylindan-5-ol

HRID 442476Notes

Reaction equation

HRID 442476 reaction equation
OC1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([Cl:18])[CH:12]=2)([CH3:10])[CH3:9])=CC=1Cl.[CH3:20]C(=C)C>C1(C)C=CC=CC=1>[OH:17][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][C:13]=1[Cl:18])[C:8]([CH3:9])([CH3:10])[CH2:5][C:6]2([CH3:7])[CH3:20]

Participants

4

Reactant 2

HCID 8255IsobutyleneHCID 66238Phenol, 4,4'-(1-methylethylidene)bis[2-chloro-

Product 1

HCID 1045746-Chloro-1,1,3,3-tetramethylindan-5-olYield 16.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
230 °C

Procedure

99 g (0.33 mol) of 2,2-bis-(4-hydroxy-3-chlorphenyl)-propane, 20 g of an acid-activated fuller's earth and 60 g (1.07 mol) of isobutylene are introduced into an autoclave. After stirring for 6 hours at 230° C., 200 ml of toluene are added, the catalyst is filtered off and the solvent evaporated. The residue (127.1 g) is distilled in vacuo in a packed column. 12.2 g (0.055 mol) of 5-hydroxy-6-chlor-1,1,3,3-tetramethyl indane (VII) melting at 51° C. are obtained from the fraction boiling at 75°-83° C./0.2 Torr by recrystallisation from 25 ml of petroleum ether. ##STR25##

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe solvent evaporated
  3. distillationThe residue (127.1 g) is distilled in vacuo in a packed column

Sources & evidence

ORD record
ord-ecce052c40ed446ab0de6e7e0405f77e
Source dataset
uspto-grants-1977_08
Patent number
US04045499

Reaction notes

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