Toluene → 4-Phenyl-2,3-dihydro-1H-inden-2-ol

HRID 67817

Reaction equation

HRID 67817 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4](S(O)(=O)=O)=[CH:3][CH:2]=1.[C:12]1([CH3:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH2:19].[C:20]1(C)C=CC=CC=1>>[C:1]1([C:11]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:17]=2[CH2:12][CH:18]([OH:19])[CH2:20]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 22272177Toluene water

Product 1

HCID 129423884-Phenyl-2,3-dihydro-1H-inden-2-ol

Procedure

A solution of the 79.6 g of oil and 0.1 g of p-toluene-sulfonic acid in 350 ml of toluene was heated at reflux for 15-20 minutes during which a toluene/water azeotrope collected in a Dean-Stark trap. The mixture was cooled, placed on a silica gel chromatography column, and eluted first with toluene, then with 1:1 toluene/ethyl acetate. Appropriate fractions were combined and concentrated to give, after crystallization from toluene, 44.5 g of 4-phenyl-2-indanol, mp 71°-73° C. The nmr spectrum was consistent with the proposed structure.

Workup

  1. customazeotrope collected in a Dean-Stark trap
  2. temperatureThe mixture was cooled
  3. washeluted first with toluene
  4. concentrationconcentrated
  5. customto give
  6. customafter crystallization from toluene, 44.5 g of 4-phenyl-2-indanol, mp 71°-73° C

Sources & evidence

ORD record
ord-479e60bff2ee413bbdf14e999444e055
Source dataset
uspto-grants-1982_08
Patent number
US04346251

Linked notes

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