3-Cyclopentoxy-4-nitrobenzyl alcohol → Benzaldehyde, 3-(cyclopentyloxy)-4-nitro-

HRID 1073741Notes

Reaction equation

HRID 1073741 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=2[N+:15]([O-:17])=[O:16])[CH2:10][OH:11])[CH2:5][CH2:4][CH2:3][CH2:2]1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=2[N+:15]([O-:17])=[O:16])[CH:10]=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 543467953-Cyclopentoxy-4-nitrobenzyl alcohol

Product 1

HCID 15052470Benzaldehyde, 3-(cyclopentyloxy)-4-nitro-

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5.0 g (21.1 mmol) of 3-cyclopentoxy-4-nitrobenzyl alcohol in 200 mL of dry methylene chloride is added 19.0 g (218.5 mmol) of activated manganese dioxide in one portion. The brown suspension is warmed to reflux for 48 hours after which time the mixture is cooled to room temperature, filtered over Celite 545 and concentrated. Liquid chromatography over 200 g of silica gel eluting with 30% ethyl acetate in hexane provided the desired, analytically pure compound upon drying in vacuo.

Workup

  1. temperatureThe brown suspension is warmed
  2. temperatureto reflux for 48 hours after which time the mixture
  3. filtrationfiltered over Celite 545
  4. concentrationconcentrated
  5. customLiquid chromatography over 200 g of silica gel eluting with 30% ethyl acetate in hexane provided the
  6. customanalytically pure compound upon drying in vacuo

Sources & evidence

ORD record
ord-26154889509f41b28f52a27f3dd1b964
Source dataset
uspto-grants-1990_11
Patent number
US04971959

Reaction notes

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