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 1288256노트

반응식

HRID 1288256 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of 2.5 g. (0.011 mole) of 5-(3-methyl-2-octyl)resorcinol and 2.0 g. (0.013 mole) of methyl 3-oxo-2,3,4,5-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. Amer. Chem. Soc. 70, 664-8 (1948)). The reaction mixture was allowed to stand for three 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.

후처리

  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

출처 및 근거

ORD 기록
ord-59bee94b02c64c748a24707caf5cbcde
출처 데이터셋
uspto-grants-1976_10
특허 번호
US03987190

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