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

HRID 1867245Notes

Reaction equation

HRID 1867245 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-fef5663a8e664824a8669e85124167dc
Source dataset
uspto-grants-2009_12
Patent number
US07632830B2

Reaction notes

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