2-Chloro-4-t-butylbenzyl alcohol → 4-tert-Butyl-2-chlorobenzaldehyde

HRID 859870Notes

Reaction equation

HRID 859870 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]=[CH:6][C:3]=1[CH2:4][OH:5]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

4

Reactant 1

HCID 688990782-Chloro-4-t-butylbenzyl alcohol

Product 1

HCID 178596104-tert-Butyl-2-chlorobenzaldehydeYield 79%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

The alcohol compound (195 mg, 0.981 mmol) obtained in Step 1-3 was dissolved in chloroform (5 ml). Activated manganese dioxide (1.27 g) was added to the obtained solution, and they were violently stirred at 50° C. for 2 hours. After leaving to cool, manganese dioxide was filtered out, and the filtrate was concentrated under reduced pressure. After the purification by the silica gel column chromatography, 2-chloro-4-t-butylbenzaldehyde (yield: 152 mg, 79%) was obtained.

Workup

  1. customAfter leaving
  2. temperatureto cool
  3. filtrationmanganese dioxide was filtered out
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customAfter the purification by the silica gel column chromatography

Sources & evidence

ORD record
ord-ea9a6c7d221d4ca8b889436e865a4da8
Source dataset
uspto-grants-2006_12
Patent number
US07153850B2

Reaction notes

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