HCID 18690776, compound → HCID 18350561, compound

HRID 741577Notes

Reaction equation

HRID 741577 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[C:12]([C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[CH2:21][CH:20]([CH2:25][OH:26])[CH2:19]2)([CH3:15])([CH3:14])[CH3:13]>ClCCl.CCOCC>[C:12]([C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[CH2:21][CH:20]([CH:25]=[O:26])[CH2:19]2)([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 2

HCID 18690776HCID 18690776, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 18350561HCID 18350561, compoundYield 72.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of pyridinium chlorochromate (PCC, Fluka, 3.24 g, 15 mmole) in dichloromethane (20ml), there was added at room temperature, a solution of 5-tert-butyl-2-indanmethanol (2.04 g, 10 mmole) in dichloromethane (10 ml). The mixture was stirred for 5 h at room temperature. It was diluted in ether (50 ml), filtered on CELITE®, then on a FLORISIL® column (Fluka), and concentrated. Bulb-to-bulb distillation provided 5-tert-butyl-2-indancarbaldehyde (1.47 g, purity>99%, yield 72%) as a colorless oil.

Workup

  1. additionwas added at room temperature
  2. filtrationfiltered on CELITE®
  3. concentrationon a FLORISIL® column (Fluka), and concentrated
  4. distillationBulb-to-bulb distillation

Sources & evidence

ORD record
ord-f57a5e052b364cd9ac0b94b9dbf61bb3
Source dataset
uspto-grants-1996_09
Patent number
US05552379

Reaction notes

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