Oxygen → 3,5-Dimethyl-4-hydroxybenzaldehyde

HRID 2073153Notes

Reaction equation

HRID 2073153 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].[O:11]=O>[Pt].C(O)(=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10])[CH:8]=[O:11]

Participants

5

Reactant 2

HCID 977OxygenHCID 106982,4,6-Trimethylphenol

Product 1

HCID 752223,5-Dimethyl-4-hydroxybenzaldehydeYield 75%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
75 °C

Procedure

Into a 300-ml stainless steel Parr bomb is placed 25 g of 2,4,6-trimethylphenol, 2.0 g of 5 percent platinum on carbon and 75 ml of acetic acid. The bomb is pressurized to 250 psig with O2 and heated to 75° C. The bomb is held at this temperature for 4.5 hours. The material is filtered through celite and the acetic acid is removed by rotary evaporation. A 75 percent yield of 3,5-dimethyl-4-hydroxybenzaldehyde is obtained. This material is further purified using a toluene slurry wash (m.p. 111° C.-113° C.). The principle by-product is 2,6-dimethyl p-benzoquinone.

Workup

  1. filtrationThe material is filtered through celite
  2. customthe acetic acid is removed by rotary evaporation

Sources & evidence

ORD record
ord-779bd3a8eea045d8b28d2c4893467d90
Source dataset
uspto-grants-1990_04
Patent number
US04915875

Reaction notes

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