1-(2-Hydroxy-4,6-dimethylphenyl)-1-butanone → 2-Butyl-3,5-dimethylphenol

HRID 542351Notes

Reaction equation

HRID 542351 reaction equation
[C:1]([C:6]1[C:11]([CH3:12])=[CH:10][C:9]([CH3:13])=[CH:8][C:7]=1[OH:14])(=O)[CH2:2][CH2:3][CH3:4].[H][H]>Cl(O)(=O)(=O)=O.[Pt]=O.C(O)(=O)C>[CH2:1]([C:6]1[C:11]([CH3:12])=[CH:10][C:9]([CH3:13])=[CH:8][C:7]=1[OH:14])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 2

HCID 42010061-(2-Hydroxy-4,6-dimethylphenyl)-1-butanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 202099972-Butyl-3,5-dimethylphenol

Reagents, catalysts & solvents 3

HCID 24247Perchloric AcidCatalystHCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

10 g. of 2-butyryl-3,5-dimethyl-phenol are dissolved in 100 ml. of glacial acetic acid. After the addition of 3 drops of perchloric acid, the solution is hydrogenated under normal conditions in the presence of 0.5 g. of platinum oxide. After the uptake of 3.0 l. of hydrogen, the hydrogenation is stopped. The catalyst is filtered off. The filtrate is extracted with ether. The ether extract is washed with water to neutral reacton, dried over sodium sulfate and evaporated. There is obtained 2-butyl-3,5-dimethyl-phenol, which melts at 65°-67° C. after absorption on silica gel, using methylene chloride/hexane 1:1 parts by volume as the eluent.

Workup

  1. filtrationThe catalyst is filtered off
  2. extractionThe filtrate is extracted with ether
  3. extractionThe ether extract
  4. washis washed with water to neutral reacton
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-ce299e965579469ca6c92cdc6b259782
Source dataset
uspto-grants-1987_04
Patent number
US04656310

Reaction notes

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