Formaldehyde → HCID 13345181, Verbindung

HRID 1462316Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1462316
[C:1]([C:5]1[CH:18]=[CH:17][C:16]2[S:15][C:14]3[C:9](=[CH:10][C:11]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:12][CH:13]=3)[CH2:8][C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[CH2:28]=[O:29].OS(O)(=O)=O>C1COCC1>[C:1]([C:5]1[CH:18]=[CH:17][C:16]2[S:15][C:14]3[C:9](=[CH:10][C:11]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:12][CH:13]=3)[CH:8]([CH2:28][OH:29])[C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 133451792,7-Di-tert-butyl-9H-thioxantheneHCID 178418339Butyllithium

Produkt 1

HCID 13345181HCID 13345181, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 15 g of 2,7-di-t-butylthioxanthene in 150 mL of dry THF cooled to -75°, mL of n-butyl lithium solution (2.45 M) was added dropwise. A deep red color developed. After stirring at -75° for 30 min., 5 g of paraformaldehyde was added slowly. The mixture was then allowed to warm to room temperature and refluxed for 30 min. Completion of the reaction was signaled by discharge of the red color. The mixture, which contained a gray precipitate, was cooled and decomposed with ice and 25% H2SO4. Extraction of the aqueous layer with CH2Cl2, followed by washing of the extracts with H2O and saturated NaCl solution, drying over (MgSO4) and then evaporation gave an oily material which was purified by chromatography on silica gel by elution with hexane-ethyl acetate (95/5). The alcohol was obtained as a white solid, m.p. 158°-159°. Anal. calculated for C22H28OS: C, 77.64; H, 8.13; S, 9.41. Found: C, 77.72; H, 8.52; S, 9.28.

Aufarbeitung

  1. temperaturerefluxed for 30 min
  2. temperaturewas cooled
  3. extractionExtraction of the aqueous layer with CH2Cl2
  4. washby washing of the extracts with H2O and saturated NaCl solution
  5. dry with materialdrying over (MgSO4)
  6. customevaporation
  7. customgave an oily material which
  8. customwas purified by chromatography on silica gel by elution with hexane-ethyl acetate (95/5)

Quellen und Nachweise

ORD-Eintrag
ord-a9950af6975749e4aec29a8e8273f4dc
Quelldatensatz
uspto-grants-1984_07
Patentnummer
US04460501

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