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

HRID 613999ノート

反応式

HRID 613999 の反応式
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

参加物

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8df4405deeaf4a7b931346688ed3dcde
出典データセット
uspto-grants-1979_03
特許番号
US04143055

反応ノート

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