Hydrochloric Acid → Phenol, 2,4-dimethoxy-3-methyl-

HRID 352342Notes

Reaction equation

HRID 352342 reaction equation
[CH3:1][O:2][C:3]1[C:10]([CH3:11])=[C:9]([O:12][CH3:13])[CH:8]=[CH:7][C:4]=1C=O.ClC1C=CC=C(C(OO)=[O:22])C=1.[OH-].[K+].Cl>ClCCl.O>[CH3:1][O:2][C:3]1[C:10]([CH3:11])=[C:9]([O:12][CH3:13])[CH:8]=[CH:7][C:4]=1[OH:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 2516932,4-Dimethoxy-3-methylbenzaldehyde

Product 1

HCID 10975869Phenol, 2,4-dimethoxy-3-methyl-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To 416 mmol of 2,4-dimethoxy-3-methyl-benzaldehyde dissolved in 200 ml of dichloromethane there are added 624 mmol of meta-chloroperbenzoic acid. The reaction mixture is heated at reflux for 5 hours before being filtered. The filtrate is washed three times using 200 ml of saturated NaHCO3 solution each time and then dried over magnesium sulphate. After evaporating off the solvent, the crude product is taken up in 400 ml of methanol. 624 mmol of 10% KOH solution are added. The mixture is stirred for one hour and is then adjusted to pH=4 using 1N hydrochloric acid solution. After stirring for one hour, the volume is reduced to ⅓. The crude product is taken up in 400 ml of water and extracted with dichloromethane. The organic phases are collected and dried. After evaporating off the solvents, the residue obtained is purified by chromatography on a silica column (eluant: cyclohexane/ethyl acetate 90/10) to yield the expected product.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 5 hours
  3. filtrationbefore being filtered
  4. washThe filtrate is washed three times
  5. dry with materialdried over magnesium sulphate
  6. customAfter evaporating off the solvent
  7. stirringAfter stirring for one hour
  8. extractionextracted with dichloromethane
  9. customThe organic phases are collected
  10. customdried
  11. customAfter evaporating off the solvents
  12. customthe residue obtained
  13. customis purified by chromatography on a silica column (eluant: cyclohexane/ethyl acetate 90/10)

Sources & evidence

ORD record
ord-c646473d9a4e4b7b9283acf433afd770
Source dataset
uspto-grants-2004_06
Patent number
US06747032B2

Reaction notes

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