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

HRID 423267노트

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HRID 423267 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
120 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-79cc7ff0846244c5bf0479f0ddb3d9ce
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101774B2

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