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

HRID 1356980Notes

Reaction equation

HRID 1356980 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 for 1 hour, 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-4b560857d45c41ee84e9967d88474124
Source dataset
uspto-grants-2003_07
Patent number
US06589914B2

Reaction notes

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