2-Hydroxy-5-methylbenzyl alcohol → Benzaldehyde, 2-hydroxy-5-methyl-

HRID 1739486

Reaction equation

HRID 1739486 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[OH:10]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[OH:10][C:4]1[CH:5]=[CH:6][C:7]([CH3:9])=[CH:8][C:3]=1[CH:2]=[O:1]

Participants

4

Reactant 1

HCID 2574522-Hydroxy-5-methylbenzyl alcohol

Product 1

HCID 69184Benzaldehyde, 2-hydroxy-5-methyl-Yield 20.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

2-Hydroxymethyl-4-methylphenol (3.1 g, 22.4 mMol) was dissolved in CHCl3 (95 ml). The solution was treated with manganese dioxide (8.7 g, 100 mmol) and the reaction stirred at ambient temperature overnight under an argon atmosphere. The reaction was then filtered through Celite and the solvent evaporated. The residue was subjected to chromatography (eluant: ethyl ether/hexane) to give 2-hydroxy-5-methylbenzaldehyde as a pale green solid (0.63 g, 20.7%).

Workup

  1. filtrationThe reaction was then filtered through Celite
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-d860a9483f7040eca836722a1bc22f20
Source dataset
uspto-grants-1999_10
Patent number
US05965741

Linked notes

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