Methyl 4-Allyl-3-hydroxy-5-methoxybenzoate → 2,3-Dihydro-4-methoxy-2-methyl-6-benzofurancarboxylic acid

HRID 613999노트

반응식

HRID 613999 반응식
C[O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([CH2:12][CH:13]=[CH2:14])=[C:6]([OH:15])[CH:5]=1>C(O)(=O)C>[CH3:11][O:10][C:8]1[C:7]2[CH2:12][CH:13]([CH3:14])[O:15][C:6]=2[CH:5]=[C:4]([C:3]([OH:2])=[O:16])[CH:9]=1

참가 물질

3

반응물 1

HCID 53889137Methyl 4-Allyl-3-hydroxy-5-methoxybenzoate

생성물 1

HCID 213298312,3-Dihydro-4-methoxy-2-methyl-6-benzofurancarboxylic acid수율 60%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

1 gram of 4-allyl-3-hydroxy-5-methoxybenzoic acid methyl ester in 5 cc of glacial acetic acid and 1.5 cc of 48%HBR is refluxed for 3 hours. After this time the mixture is concentrated to dryness and the crude residue is dissolved in an aqueous alkali solution. 0.3 grams of dimethyl sulfate are added to the resulting solution which is refluxed for two additional hours. The compound of the title which precipitates upon acidification of the cooled reaction mixture is recrystallized from ethyl ether-petroleum ether. Yield 60%. M.p. 180°-182° C.

후처리

  1. concentrationAfter this time the mixture is concentrated to dryness
  2. dissolutionthe crude residue is dissolved in an aqueous alkali solution
  3. addition0.3 grams of dimethyl sulfate are added to the resulting solution which
  4. temperatureis refluxed for two additional hours
  5. customThe compound of the title which precipitates upon acidification of the cooled reaction mixture
  6. customis recrystallized from ethyl ether-petroleum ether

출처 및 근거

ORD 기록
ord-8df4405deeaf4a7b931346688ed3dcde
출처 데이터셋
uspto-grants-1979_03
특허 번호
US04143055

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