4-Benzyloxy-3-chloro-5-methyl-1-benzoyloxybenzene → 4-Benzoyloxy-2-chloro-6-methylphenol

HRID 582349Notes

Reaction equation

HRID 582349 reaction equation
C([O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([O:16][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:11][C:10]=1[Cl:25])C1C=CC=CC=1.[H][H]>[C].[Pd].C(OCC)(=O)C>[C:17]([O:16][C:12]1[CH:13]=[C:14]([CH3:15])[C:9]([OH:8])=[C:10]([Cl:25])[CH:11]=1)(=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 185045544-Benzyloxy-3-chloro-5-methyl-1-benzoyloxybenzeneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 185045884-Benzoyloxy-2-chloro-6-methylphenolYield 96%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A reaction vessel was charged with 35 g of 4-benzyloxy-3-chloro-5-methyl-1-benzoyloxybenzene and 200 ml of ethyl acetate, and the air in the vessel was replaced with nitrogen. Then, 2 g of 10% palladium carbon was added, and the nitrogen in the vessel was replaced with hydrogen, followed by vigorous stirring at room temperature for 10 hours. The hydrogen in the vessel was replaced with nitrogen, after which the reaction mixture was filtered, and the filtrate was concentrated. The residue was subjected to silica gel chromatography, which afforded 25 g of 4-benzoyloxy-2-chloro-6-methylphenol (96% yield).

Workup

  1. filtrationafter which the reaction mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-cde6e5af6ae9412cb5c65f73f1afcaf1
Source dataset
uspto-grants-1999_07
Patent number
US05922880

Reaction notes

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