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Water → HCID 53703941, Verbindung

HRID 1701163
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1701163
[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:16]([CH2:18][C:19]([OH:21])=[O:20])=[O:17])[CH3:15])=[CH:10][CH:9]=1.[C:22]1(C)C=CC(S(O)(=O)=O)=CC=1.O>CO.COC(OC)(C)C>[CH3:22][O:20][C:19](=[O:21])[CH2:18][S:16]([CH:14]([C:11]1[CH:12]=[CH:13][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])=[CH:9][CH:10]=1)[CH3:15])=[O:17]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 20348737HCID 20348737, Verbindung

Produkt 1

HCID 53703941HCID 53703941, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 64952,2-Dimethoxypropane
Lösungsmittel

Versuchsvorschrift

1.5 gm (50 millimols) of [1-(2'-fluoro-4-biphenylyl)-ethylsulfinyl]-acetic acid, m.p. 164°-165° C., were dissovled in 3 ml of methanol and 1.2 ml of 2,2-dimethoxypropane, 100 mgm of p-toluenesulfonic acid were added to the solution, and the mixture was allowed to stand for 12 days at room temperature. Then, water was added and the ester was extracted with toluene. The organic extract was washed with water, dried and evaporated, and the residue was purified by chromatography on 75 gm of silicagel (grain size 0.05-0.2 mm) with cyclohexane/ethyl acetate--1/4. The combined ester--containing fractions were evaporated, and the residue was recrystallized from 3 ml of isopropanol. Yield: 800 mgm (50% of theory); m.p. 77°-79° C.

Aufarbeitung

  1. extractionthe ester was extracted with toluene
  2. extractionThe organic extract
  3. washwas washed with water
  4. customdried
  5. customevaporated
  6. customthe residue was purified by chromatography on 75 gm of silicagel (grain size 0.05-0.2 mm) with cyclohexane/ethyl acetate
  7. additionThe combined ester--containing fractions
  8. customwere evaporated
  9. customthe residue was recrystallized from 3 ml of isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-c44c44ba02b848a28893859cd2041a34
Quelldatensatz
uspto-grants-1980_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04191776

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