Hydrochloric Acid → Dimethyl 4-hydroxy-5-methylbenzene-1,3-dicarboxylate

HRID 423267Notes

Reaction equation

HRID 423267 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:13]=[C:12](Br)[C:11]([O:15]COC)=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1.[CH3:20][Zn]C.CCCCCC.Cl>O1CCOCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:13]=[C:12]([CH3:20])[C:11]([OH:15])=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 666771415-Bromo-4-methoxymethoxyisophthalic acid dimethyl esterHCID 178443919HCID 178443919, compound

Product 1

HCID 29924533Dimethyl 4-hydroxy-5-methylbenzene-1,3-dicarboxylate

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 5-bromo-4-methoxymethoxyisophthalic acid dimethyl ester (6.00 g) in dioxane (60 mL) were added [1,1′ bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (1:1) (600 mg) and 1M dimethylzinc/hexane solution (20 mL), and the mixture was stirred at 120° C. for 5.5 hours under heating. The reaction solution was allowed to stand for cooling down to room temperature, and 1M hydrochloric acid (40 mL) was added dropwise thereto. After the reaction solution was diluted with ethyl acetate (100 mL), the insoluble material was filtered through a Celite pad. The organic layer was separated, washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=9:1, v/v) to give the title compound (2.97 g).

Workup

  1. temperatureunder heating
  2. temperaturefor cooling down to room temperature
  3. filtrationthe insoluble material was filtered through a Celite pad
  4. customThe organic layer was separated
  5. washwashed successively with water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography on silica gel (hexane

Sources & evidence

ORD record
ord-79cc7ff0846244c5bf0479f0ddb3d9ce
Source dataset
uspto-grants-2012_01
Patent number
US08101774B2

Reaction notes

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