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

HRID 2052787Notes

Reaction equation

HRID 2052787 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-27fb604fb5af4837a01fa0452c05b2b7
Source dataset
uspto-grants-2008_02
Patent number
US07326701B2

Reaction notes

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