Hydrochloric Acid → Methyl 2-allyloxy-3-formyl-4-methoxybenzoate

HRID 1370163노트

반응식

HRID 1370163 반응식
[CH2:1](Br)[CH:2]=[CH2:3].[OH-].[K+].[OH:7][C:8]1[C:17]([CH:18]=[O:19])=[C:16]([O:20][CH3:21])[CH:15]=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11].Cl>CS(C)=O>[CH2:1]([O:7][C:8]1[C:17]([CH:18]=[O:19])=[C:16]([O:20][CH3:21])[CH:15]=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11])[CH:2]=[CH2:3]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 14797Potassium HydroxideHCID 219335993-Formyl-2-hydroxy-4-methoxy-benzoic acid methyl ester

생성물 1

HCID 21933587Methyl 2-allyloxy-3-formyl-4-methoxybenzoate수율 36%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

At room temperature, 23.2 g (0.192 mol) of allyl bromide were added dropwise to a mixture of 21.0 g (0.375 mol) of potassium hydroxide and 20.2 g (0.096 mol) of methyl 2-hydroxy-3-formyl-4-methoxybenzoate in 500 ml of dimethyl sulfoxide, and the mixture was stirred at room temperature for 4 hours. The mixture was subsequently added to 1.5 l of 3% strength aqueous hydrochloric acid with stirring and extracted with ethyl acetate. The combined organic phases were washed with water and dried, and the solvent was removed. Chromatography over silica gel using cyclohexane/ethyl acetate=1:2 gave 7.7 g (36% of methyl 2-allyloxy-3-formyl-4-methoxybenzoate in the form of a yellowish oil.

후처리

  1. stirringwith stirring
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phases were washed with water
  4. customdried
  5. customthe solvent was removed

출처 및 근거

ORD 기록
ord-18550df5653244d5a1c3a918df1d680d
출처 데이터셋
uspto-grants-2003_06
특허 번호
US06583089B1

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