Toluene → 1H-Indene-2-methanol, 2,3-dihydro-2,5-dimethyl-

HRID 430423Notes

Reaction equation

HRID 430423 reaction equation
[C:1]([O-:4])([O-])=O.[K+].[K+].C1(C)C=CC=CC=1.[CH3:14][CH:15]1[CH2:23][C:22]2[C:17](=[CH:18][C:19]([CH3:24])=[CH:20][CH:21]=2)[C:16]1=O>O>[CH3:14][C:15]1([CH2:1][OH:4])[CH2:16][C:17]2[C:22](=[CH:21][CH:20]=[C:19]([CH3:24])[CH:18]=2)[CH2:23]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 115934772,6-dimethyl-2,3-dihydroinden-1-one

Product 1

HCID 113673061H-Indene-2-methanol, 2,3-dihydro-2,5-dimethyl-Yield 215.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

147.53 g of K2CO3, 875 g of toluene and 350 g of 2,6-dimethyl indanone were introduced, under nitrogen, into a Schmizo-type 1.5 l vessel provided with a condenser and a mechanical stirrer. The mixture was heated to 51°. 122.45 g of Formcel® 55% (origin: Hoechst) were then added over a period of 1 h. The mixture was stirred continuously at 51° for 2 h. The reaction medium was then cooled to 24° and 350 g of water were added. After being stirred for 10 mins, the mixture was decanted, then washed 3 times with water. Concentration in vacuo produced 404.71 g of raw product pure to 97.6% (GC).

Workup

  1. customprovided with a condenser and a mechanical stirrer
  2. temperatureThe mixture was heated to 51°
  3. addition122.45 g of Formcel® 55% (origin: Hoechst) were then added over a period of 1 h
  4. temperatureThe reaction medium was then cooled to 24°
  5. stirringAfter being stirred for 10 mins
  6. customthe mixture was decanted
  7. washwashed 3 times with water
  8. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-1d790f65d8d74beca2c6a2b617e57c72
Source dataset
uspto-grants-2001_11
Patent number
US06323173B1

Reaction notes

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