Toluene → 1,1,2,3,3-pentamethyl-2,3,4,5,6,7-hexahydro-1H-inden-4-ol

HRID 463528Notes

Reaction equation

HRID 463528 reaction equation
[CH3:1][CH:2]([CH3:4])[O-:3].[Al+3].[CH3:6][CH:7]([CH3:9])[O-].[CH3:10][CH:11]([CH3:13])[O-].[C:14]1([CH3:20])[CH:19]=[CH:18]C=C[CH:15]=1>>[CH3:6][C:7]1([CH3:9])[C:13]2[CH2:11][CH2:10][CH2:4][CH:2]([OH:3])[C:1]=2[C:14]([CH3:15])([CH3:20])[CH:19]1[CH3:18]

Participants

3

Reactant 2

HCID 1140TolueneHCID 11143Aluminum isopropoxide3×

Product 1

HCID 148178411,1,2,3,3-pentamethyl-2,3,4,5,6,7-hexahydro-1H-inden-4-ol

Procedure

Into a 2-liter reaction vessel are placed 831 ml of toluene and 226.9 grams (1.11 moles) of aluminum isopropoxide. The mixture is heated to reflux and while refluxing, over a one hour period, tetrahydro pentamethylindane epoxide having the structure: ##STR63## is added to the reaction mass. The reaction mass is continued to be refluxed for a period of twelve hours while being monitored by GLC analysis. An additional 0.5 moles of aluminum isopropoxide is added (101.5 grams) at the end of the twelve hour period and the refluxing is continued for an additional eight hours. At the end of the twenty hour period, an additional 50.7 grams of aluminum triisopropylate is added and the reaction mass is continued to be refluxed for an additional twenty two hours (total reflux time 42 hours).

Workup

  1. customInto a 2-liter reaction vessel
  2. temperatureThe mixture is heated
  3. temperatureto reflux
  4. temperaturewhile refluxing, over a one hour period
  5. temperatureto be refluxed for a period of twelve hours
  6. temperatureto be refluxed for an additional twenty two hours (total reflux time 42 hours)

Sources & evidence

ORD record
ord-53c92a33ee9048e986d9b421ff4be77a
Source dataset
uspto-grants-1985_05
Patent number
US04520032

Reaction notes

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