2-Thiophenecarboxylic acid, tetrahydro-3-oxo-, methyl ester → 1,2-Dihydro-9-hydroxy-7-(3-methyl-2-octyl)-4-oxo-4H-thieno[2,3-c][1]benzopyran

HRID 1282840ノート

反応式

HRID 1282840 の反応式
[CH3:1][CH:2]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:3]([C:5]1[CH:6]=[C:7]([OH:12])[CH:8]=[C:9]([CH:11]=1)[OH:10])[CH3:4].O=[C:19]1[CH2:23][CH2:22][S:21][CH:20]1[C:24](OC)=[O:25]>C(O)C>[OH:10][C:9]1[C:8]2[C:19]3[CH2:23][CH2:22][S:21][C:20]=3[C:24](=[O:25])[O:12][C:7]=2[CH:6]=[C:5]([CH:3]([CH:2]([CH3:1])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH3:4])[CH:11]=1

参加物

4

反応物 2

HCID 1028702-Thiophenecarboxylic acid, tetrahydro-3-oxo-, methyl esterHCID 2581765-(3-Methyloctan-2-yl)benzene-1,3-diol

生成物 1

HCID 214339001,2-Dihydro-9-hydroxy-7-(3-methyl-2-octyl)-4-oxo-4H-thieno[2,3-c][1]benzopyran

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of 2,5 g. (0.011 mole) of 5-(3-methyl-2-octyl)resorcinol and 2.0 g. (0.013 mole) of the methyl 3-oxo2,3,4,5-tetrahydrothiophene-2-carboxylate in 50 ml. of absolute ethanol in a three-necked flask equipped with drying tube was cooled in an ice-water bath and saturated with dry hydrogen chloride. The 5-(3-methyl-2-octyl) resorcinol was prepared according to the method of Adams, MacKenzie and Loewe (J. Am. Chem. Soc. 70, 664-8 (1948). The reaction mixture was allowed to stand for 3 days at room temperature, during which time a heavy yellow solid formed. The hydrogen chloride was evaporated, the mixture was concentrated and the solid was filtered and washed with ethanol. The yield of the crude benzopyrone thus obtained was 2.6 g. (59%), m.p. 190°-205°C.

後処理

  1. customwith drying tube
  2. temperaturewas cooled in an ice-water bath and saturated with dry hydrogen chloride
  3. customThe 5-(3-methyl-2-octyl) resorcinol was prepared
  4. customa heavy yellow solid formed
  5. customThe hydrogen chloride was evaporated
  6. concentrationthe mixture was concentrated
  7. filtrationthe solid was filtered
  8. washwashed with ethanol

出典と根拠

ORDレコード
ord-7327093738294755852767f0ea1f4d6d
出典データセット
uspto-grants-1976_08
特許番号
US03972880

反応ノート

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