Hydrochloric Acid → Benzoic acid, 2,4-dimethoxy-, methyl ester

HRID 501784

반응식

HRID 501784 반응식
OC1C=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=O.[C:12](=O)([O-])[O-].[K+].[K+].S([O:23][CH3:24])(OC)(=O)=O.Cl.[C:26]([O:29][CH2:30]C)(=[O:28])[CH3:27]>O.CN(C)C=O>[CH3:12][O:11][C:9]1[CH:8]=[C:7]([O:23][CH3:24])[CH:3]=[CH:4][C:27]=1[C:26]([O:29][CH3:30])=[O:28]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 14912,4-Dihydroxybenzoic AcidHCID 6497Dimethyl Sulfate2회HCID 8857Ethyl AcetateHCID 11430Potassium Carbonate2회

생성물 1

HCID 137451Benzoic acid, 2,4-dimethoxy-, methyl ester

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
75 °C

실험 절차

50 g of 2,4-dihydroxybenzoic acid, 269 g of potassium carbonate, 123 mL of dimethyl sulfate, and 500 mL of N,N-dimethylformamide were suspended together, and this suspension was stirred for 6.5 hours at 70 to 80° C. Further, 90 g of potassium carbonate and 61 mL of dimethyl sulfate were added to this suspension, which was stirred for another 4 hours at 110 to 115° C. This reaction mixture was added to a mixture of ethyl acetate and water, and adjusted to pH 2 with 6M hydrochloric acid, and then the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure. The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=1:2] to yield 54 g of methyl 2,4-dimethoxybenzoate as yellow oil.

후처리

  1. stirringwas stirred for another 4 hours at 110 to 115° C
  2. customthe organic phase was separated
  3. washAfter the resultant organic phase was washed with water
  4. dry with materiala saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled out under reduced pressure
  6. customThe resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=1:2]

출처 및 근거

ORD 기록
ord-fb59e1c798564fa39839988088ff206f
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772285B2

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