Acetyl chloride → 1-[2,3-Dihydro-1,1,2,6-tetramethyl-3-(1-methylethyl)-1H-inden-5-yl]ethanone

HRID 223115Notes

Reaction equation

HRID 223115 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH:5]([CH:8]1[C:16]2[C:11](=[CH:12][C:13]([CH3:17])=[CH:14][CH:15]=2)[C:10]([CH3:19])([CH3:18])[CH:9]1[CH3:20])([CH3:7])[CH3:6].[C:21](Cl)(=[O:23])[CH3:22]>[N+](C)([O-])=O>[C:21]([C:14]1[CH:15]=[C:16]2[C:11]([C:10]([CH3:19])([CH3:18])[CH:9]([CH3:20])[CH:8]2[CH:5]([CH3:7])[CH3:6])=[CH:12][C:13]=1[CH3:17])(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 30178881,1,2,6-Tetramethyl-3-(propan-2-yl)-2,3-dihydro-1H-indeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 916961-[2,3-Dihydro-1,1,2,6-tetramethyl-3-(1-methylethyl)-1H-inden-5-yl]ethanoneYield 95%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

At 0°-5° C. a solution of 4 g AlCl3 in 50 ml nitromethane is added to a mixture of 6 g 1-isopropyl-2,3,3,5-tetramethyl indan (obtained according to example I or II) and 25 g acetyl chloride. Then the reaction mixture is stirred at room temperature during 30 min. and poured out into ice and extracted three times with ether. The solution in ether is washed neutral, dried and evaporated. The residue is distilled under diminished pressure to obtain 6-acetyl-1-isopropyl-2,3,3,5-tetramethyl indan in a yield of 95%. B.p. 144°-146° C./1 mm Hg; n20D =1,5301.

Workup

  1. additionpoured out into ice
  2. extractionextracted three times with ether
  3. washThe solution in ether is washed neutral
  4. customdried
  5. customevaporated
  6. distillationThe residue is distilled under diminished pressure

Sources & evidence

ORD record
ord-f96771aa827f497dbcba7967e29ea870
Source dataset
uspto-grants-1982_10
Patent number
US04352748

Reaction notes

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