Hydrochloric Acid → 3,5-Dimethoxy-4-methylphenol

HRID 2359191Notes

Reaction equation

HRID 2359191 reaction equation
C([O:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([CH3:12])=[C:6]([O:13][CH3:14])[CH:5]=1)=O.C([O-])([O-])=O.[K+].[K+].Cl>CO.O>[CH3:14][O:13][C:6]1[CH:5]=[C:4]([OH:3])[CH:9]=[C:8]([O:10][CH3:11])[C:7]=1[CH3:12]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 86657502HCID 86657502, compound

Product 1

HCID 106071943,5-Dimethoxy-4-methylphenolYield 29%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 3,5-dimethoxy-4-methylphenyl formate (2.9 g, 14.8 mmol) in wet MeOH (81 mL) was added K2CO3 (8.1 g, 58.6 mmol). The mixture was stirred for 2 hrs at room temperature then H2O (2-3 mL) was added. After stirring for 21 hrs, the mixture was diluted with H2O, acidified with 6M HCl to pH 3-4, and extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (0-35% EtOAc-hexanes) gave 3,5-dimethoxy-4-methylphenol as an impure yellow powder (0.71 g, 29% yield).

Workup

  1. stirringAfter stirring for 21 hrs
  2. extractionextracted with EtOAc
  3. washThe combined organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography (0-35% EtOAc-hexanes)

Sources & evidence

ORD record
ord-41c1d478c11a4649ac9b8f49550baddf
Source dataset
uspto-grants-2014_04
Patent number
US08685975B2

Reaction notes

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