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Thioglycolic Acid → HCID 20348735, Verbindung

HRID 1701158
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1701158
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH:14](O)[CH3:15])=[CH:10][CH:9]=1.FC1C=CC=CC=1C1C=CC(CC(CC2C=CC(C3C=CC=CC=3F)=CC=2)=O)=CC=1.[BH4-].[Na+].[SH:49][CH2:50][C:51]([OH:53])=[O:52].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.C1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([S:49][CH2:50][C:51]([OH:53])=[O:52])[CH3:15])=[CH:10][CH:9]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 1133Thioglycolic AcidHCID 6101p-Toluenesulfonic acidHCID 4311764Sodium borohydrideHCID 13519938HCID 13519938, VerbindungHCID 544884792'-Fluoro-4-biphenylyl-methyl-ketone

Produkt 1

HCID 20348735HCID 20348735, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 241BenzeneLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

50 gm (0.23 mol) of 1-(2'-fluoro-4-biphenylyl)-1-hydroxy-ethane, m.p. 88° C., (prepared from 2'-fluoro-4-biphenylyl-methyl-ketone by reduction with sodium borohydride in methanol) were dissolved in 500 ml of benzene, 32.2 gm (0.276 mol) of 80% mercapto-acetic acid and 1 gm of p-toluenesulfonic acid were added, and the mixture was heated at its boiling point for 1 hour, using an apparatus equipped with a water trap. 20.5 ml of water were separated. The benzene solution was washed with water after cooling, dried and evaporated. The crystalline residue was recrystallized from benzene/cyclohexane (2:1), whereby 38.0 gm (61.5% of theory) of the title compound, m.p. 125°-127° C., were obtained.

Aufarbeitung

  1. temperaturethe mixture was heated at its boiling point for 1 hour
  2. customequipped with a water trap
  3. custom20.5 ml of water were separated
  4. washThe benzene solution was washed with water
  5. temperatureafter cooling
  6. customdried
  7. customevaporated
  8. customThe crystalline residue was recrystallized from benzene/cyclohexane (2:1), whereby 38.0 gm (61.5% of theory) of the title compound, m.p. 125°-127° C.
  9. customwere obtained

Quellen und Nachweise

ORD-Eintrag
ord-f4501e07a2e4490f942fc150eeaaa7a7
Quelldatensatz
uspto-grants-1980_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04191776

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