Potassium Hydroxide → 3-Chloro-4-methoxymethoxy-5-methylphenol

HRID 363109Notes

Reaction equation

HRID 363109 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:13]C(=O)C2C=CC=CC=2)[CH:5]=[C:6]([CH3:12])[C:7]=1[O:8][CH2:9][O:10][CH3:11].[OH-].[K+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([OH:13])[CH:5]=[C:6]([CH3:12])[C:7]=1[O:8][CH2:9][O:10][CH3:11]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 185046333-Chloro-4-methoxymethoxy-5-methyl-1-benzoyloxybenzene

Product 1

HCID 185045733-Chloro-4-methoxymethoxy-5-methylphenolYield 101.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Then, 26 g of 3-chloro-4-methoxymethoxy-5-methyl-1-benzoyloxybenzene was dissolved in 200 ml of methanol, and the solution was stirred at room temperature, while adding dropwise 60 ml of 10% aqueous potassium hydroxide solution. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was added to 150 ml of water, neutralized with 10% aqueous hydrochloric acid solution, and extracted with 200 ml of diethyl ether. The solvent was removed by distillation under reduced pressure, and the residue was subjected to silica gel chromatography, which afforded 17.4 g of 3-chloro-4-methoxymethoxy-5-methylphenol (96% yield).

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was removed by distillation under reduced pressure
  3. additionThe residue was added to 150 ml of water
  4. extractionextracted with 200 ml of diethyl ether
  5. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-d9350658f687402faa848603fc6f059a
Source dataset
uspto-grants-1999_02
Patent number
US05872137

Reaction notes

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