4-Benzyloxy-3-ethyl-5-methylphenyl benzoate → 2-Ethyl-6-methyl-4-benzoyloxyphenol

HRID 618412Notes

Reaction equation

HRID 618412 reaction equation
[C:1]([O:9][C:10]1[CH:15]=[C:14]([CH3:16])[C:13]([O:17]CC2C=CC=CC=2)=[C:12]([CH2:25][CH3:26])[CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C(OCC)(=O)C.[Pd]>[C:1]([O:9][C:10]1[CH:15]=[C:14]([CH3:16])[C:13]([OH:17])=[C:12]([CH2:25][CH3:26])[CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 542360964-Benzyloxy-3-ethyl-5-methylphenyl benzoateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 232824092-Ethyl-6-methyl-4-benzoyloxyphenolYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Then, 8.4 g of crude 4-benzyloxy-3-ethyl-5-methylphenyl benzoate was dissolved in 100 ml of ethyl acetate, which was put into a reaction vessel, and the air in the vessel was replaced with nitrogen gas. Then, 0.5 g of 10% palladium on carbon was added, and the nitrogen gas in the vessel was replaced with hydrogen gas, followed by vigorous stirring at room temperature for 24 hours. The hydrogen gas in the vessel was replaced with nitrogen gas, after which the reaction mixture was filtered through cerite and the filtrate was concentrated under reduced pressure, which afforded 5.9 g of crude 3-ethyl-4-hydroxy-5-methylphenyl benzoate (95% yield).

Workup

  1. customwhich was put into a reaction vessel
  2. filtrationafter which the reaction mixture was filtered through cerite and the filtrate
  3. concentrationwas concentrated under reduced pressure, which

Sources & evidence

ORD record
ord-661801e440e949cf8a2eecc528767718
Source dataset
uspto-grants-1999_09
Patent number
US05952386

Reaction notes

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