Diethyl Ether → 6140-63-2

HRID 1252183Notes

Reaction equation

HRID 1252183 reaction equation
[CH3:1][C:2]1([CH2:7][OH:8])[CH2:6][CH2:5][CH2:4][CH2:3]1.[Cr:9]([Cl:13])([O-:12])(=[O:11])=[O:10].[NH+:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CCOCC>C(Cl)Cl>[Cr:9]([Cl:13])([O-:12])(=[O:11])=[O:10].[NH+:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH3:1][C:2]1([CH:7]=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 12830793(1-Methylcyclopentyl)methanolHCID 178418287HCID 178418287, compound

Product 2

HCID 110078476140-63-2HCID 178418287HCID 178418287, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Pyridinium chlorochromate was prepared by following the procedure of E. J. Corey and J. W. Suggs, Tetrahedron Letters, 31, 2647 (1975). A solution of 11.8 g of 1-methylcyclopentanemethanol in 32 ml of anhydrous methylene chloride was added to a stirred suspension of 39.2 pyridinium chlorochromate in 312 ml of methylene chloride under argon. The resultant dark mixture was stirred for 1.5 hours at ambient temperature. A portion of ether was added to the resultant mixture and then the supernatant was decanted. The remaining dark residue was rinsed several times with ether. The combined ether solutions were filtered through a short pad of Florisil. The resultant solution was concentrated by distillation of ether and then the residue was distilled at 110 mm Hg to yield 6.41 g of 1-methylcyclopentanecarboxaldehyde as a colorless oil: bp 98°-100°; nmr (CDCl3) δ 1.12 (3H, s), 1.0-2.2 (8H, m) and 9.50 ppm (1H, s).

Workup

  1. customthe supernatant was decanted
  2. washThe remaining dark residue was rinsed several times with ether
  3. filtrationThe combined ether solutions were filtered through a short pad of Florisil
  4. concentrationThe resultant solution was concentrated by distillation of ether
  5. distillationthe residue was distilled at 110 mm Hg

Sources & evidence

ORD record
ord-68262ebda8a548ad9601b64a8bbdc20c
Source dataset
uspto-grants-1988_05
Patent number
US04742080

Reaction notes

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