Aluminum(III) Chloride → HCID 20095027, compound

HRID 1770147Notes

Reaction equation

HRID 1770147 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:11]([CH:19]1[CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]1=O)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>O1CCCC1>[CH2:11]([CH:19]1[CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20]1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 11139369HCID 11139369, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20095027HCID 20095027, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Then, 1140 ml of tetrahydrofuran (THF) was placed in a 3 liter-reaction vessel. Under stirring, 361.4 g (2.7M) of anhydrous aluminum chloride was added to the above THF in 25 minutes below 20° C. To the mixture, 34.3 g (9.03×10-1M) of lithium aluminum hydride was added in 10 minutes below 20° C. Further, to the resultant mixture, a solution of 100 g (4.1×10-1M) of the above-prepared 2-octyl-1-indanone in 430 ml of THF was added dropwise in 40 minutes below 5° C., followed by stirring for 30 minutes below 5° C., and heat-refluxing for 1 hour. After the reaction, the reaction mixture was cooled and washed with ethyl acetate and water in this order to decompose the 2-octyl-1-indanone. The resultant reaction mixture was poured into 2 liters of ice water and subjected to extraction with ethyl acetate, followed by washing with saturated aqueous solution of common salt, drying with anhydrous magnesium sulfate and distilling-off of the solvent to obtain 93.0 g of 2-octylindan.

Workup

  1. stirringby stirring for 30 minutes below 5° C.
  2. temperatureheat-refluxing for 1 hour
  3. customAfter the reaction
  4. temperaturethe reaction mixture was cooled
  5. washwashed with ethyl acetate and water in this order
  6. customThe resultant reaction mixture
  7. extractionsubjected to extraction with ethyl acetate
  8. washby washing with saturated aqueous solution of common salt
  9. dry with materialdrying with anhydrous magnesium sulfate and distilling-off of the solvent

Sources & evidence

ORD record
ord-51b584cd6cb84af1a36d3e6a6824c25d
Source dataset
uspto-grants-1995_01
Patent number
US05385692

Reaction notes

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