Diethyl Ether → 2-(2,3-dihydro-1H-inden-2-yl)acetaldehyde

HRID 1289440Notes

Reaction equation

HRID 1289440 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH2:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH:13]1[CH2:21][CH2:22][OH:23].CCOCC>C(Cl)Cl>[CH2:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:12][CH:13]1[CH2:21][CH:22]=[O:23]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 103520002-(2,3-dihydro-1H-inden-2-yl)ethanolHCID 178418287HCID 178418287, compound

Product 1

HCID 113786562-(2,3-dihydro-1H-inden-2-yl)acetaldehydeYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Suspended in 220 ml of methylene chloride were 18.5 g (85.8 mmol) of pyridinium chlorochromate and 70 g of Celite (No. 545). While chilling with ice water, a solution of 4.30 g (26.6 mmol) of 2-(indan-2-yl)ethanol in 15 ml of methylene chloride was added dropwise to the suspension. After stirring the mixture for 1 hour while chilling with ice water, it was further stirred at room temperature for 2 hours. The reaction product was added with 250 ml of ether to dilute it. The diluted reaction product was passed through 100 g of silica gel layer to remove inorganic matter. The solvent was distilled off to obtain 3.97 g of (indan-2-yl)acetaldehyde as a colorless oily substance. Yield: 93%.

Workup

  1. stirringwas further stirred at room temperature for 2 hours
  2. additionto dilute it
  3. customThe diluted reaction product
  4. customto remove inorganic matter
  5. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-2b9e5f4c0a984445ba15578298d97ecd
Source dataset
uspto-grants-1998_05
Patent number
US05750524

Reaction notes

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