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

HRID 369684Notes

Reaction equation

HRID 369684 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]>[CH2:25]([C:12]1[CH:11]=[C:10]([O:9][C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:15]=[C:14]([CH3:16])[C:13]=1[OH:17])[CH3:26]

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, and the solution was put in a reaction vessel. The air in the reaction vessel was replaced with nitrogen gas. To the vessel was added 0.5 g of 10% palladium on carbon, 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, and the reaction mixture was filtered through cerite. The filtrate was concentrated under reduced pressure, which afforded 5.9 g of 2-ethyl-6-methyl-4-benzoyloxyphenol (yield, 95%).

Workup

  1. customthe solution was put in a reaction vessel
  2. filtrationthe reaction mixture was filtered through cerite
  3. concentrationThe filtrate was concentrated under reduced pressure, which

Sources & evidence

ORD record
ord-0d6f680d944c48078f4b2ec852d6ef8e
Source dataset
uspto-grants-2000_10
Patent number
US06140274

Reaction notes

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