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

HRID 1387248Notes

Reaction equation

HRID 1387248 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 stilling 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-0560c4a8cad5451baef8755fc9b89b91
Source dataset
uspto-grants-2001_07
Patent number
US06268313B1

Reaction notes

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