Hydrochloric Acid → 1,2-Dihydro-10-hydroxy-8-(3-methyl-2-octyl)-5-oxo-3H,5H-thiopyrano[2,3-c][1]benzopyran

HRID 1288257Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1288257
[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[CH2:24][CH2:23][CH2:22][S:21][CH:20]1[C:25](OC)=[O:26].Cl>C(O)C>[OH:10][C:9]1[C:8]2[C:19]3[CH2:24][CH2:23][CH2:22][S:21][C:20]=3[C:25](=[O:26])[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

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 2581765-(3-Methyloctan-2-yl)benzene-1,3-diolHCID 18379299Methyl 3-oxotetrahydrothiopyran-2-carboxylate

Produkt 1

HCID 214339161,2-Dihydro-10-hydroxy-8-(3-methyl-2-octyl)-5-oxo-3H,5H-thiopyrano[2,3-c][1]benzopyran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 14.2 g. (0.06 mole) of 5-(3-methyl-2-octyl)resorcinol and 11.1 g. (0.063 mole) of methyl 3-oxo-2,3,4,5-tetrahydro-6H-thiopyran-2-carboxylate in 90 ml. of absolute ethanol was cooled in an ice-salt bath and saturated with anhydrous hydrogen chloride. After standing for 2 days at room temperature, the ethanol was removed on a rotary evaporator. The residue was dissolved in ether, washed with sodium bicarbonate solution and dried over sodium sulfate. Evaporation of the solvent gave 28.0 g. of residue which was chromatographed using activated magnesium silicate (60-100 mesh) and graded methanol/chloroform solvent mixtures. A total of 10 g. of crude solid was obtained from the 1% methanol/chloroform fractions. The material was recrystallized twice from ethyl acetate/hexane to give 8.5 g. (40%) colorless crystals, m.p. 131°-133° C. The proposed structure was confirmed by IR and NMR spectra.

Aufarbeitung

  1. customthe ethanol was removed on a rotary evaporator
  2. dissolutionThe residue was dissolved in ether
  3. washwashed with sodium bicarbonate solution
  4. dry with materialdried over sodium sulfate
  5. customEvaporation of the solvent
  6. customgave 28.0 g
  7. customof residue which was chromatographed
  8. customof crude solid was obtained from the 1% methanol/chloroform fractions
  9. customThe material was recrystallized twice from ethyl acetate/hexane
  10. customto give 8.5 g

Quellen und Nachweise

ORD-Eintrag
ord-96e7bcd0c436409ca9c094e928782938
Quelldatensatz
uspto-grants-1976_10
Patentnummer
US03987190

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