Water → 7-Phenyl-1H-indene

HRID 1156414Notes

Reaction equation

HRID 1156414 reaction equation
[C:1]1([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH2:9][CH2:10][CH:11]3O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[C:1]1([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH2:9][CH:10]=[CH:11]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 129423854-Phenyl-2,3-dihydro-1H-inden-1-ol

Product 1

HCID 129423867-Phenyl-1H-indeneYield 96.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A stirred solution of 16.7 g (0.08 mole) of 4-phenyl-1-indanol and 0.1 g of p-toluenesulfonic acid in 180 ml of benzene was heated under reflux for one hour as by-product water was collected in a Dean-Stark trap. The reaction mixture was washed with two portions of 50 ml of a 5% aqueous solution of sodium bicarbonate, then with one portion of 50 ml of water. The organic phase was dried with magnesium sulfate, filtered, and the filtrate concentrated under reduced pressure, keeping the temperature under 50° C., to give 14.8 g of 7-phenyl-1H-indene. The nmr spectrum was consistent with the proposed structure.

Workup

  1. customwas collected in a Dean-Stark trap
  2. washThe reaction mixture was washed with two portions of 50 ml of a 5% aqueous solution of sodium bicarbonate
  3. dry with materialThe organic phase was dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customunder 50° C.

Sources & evidence

ORD record
ord-69a5eb10591443a980e0a8c19471e59c
Source dataset
uspto-grants-1982_06
Patent number
US04335252

Reaction notes

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