Sodium Hydroxide → p-[(1RS, 2RS)-1-(10-hexylthiodecyl)-6-hydroxy-1,2,3,4-tetrahydronaphth-2-yl]benzoic acid

HRID 580019Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 580019
[OH-:1].[Na+].[CH2:3]([S:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH:20]1[C:29]2[C:24](=[CH:25][C:26]([OH:30])=[CH:27][CH:28]=2)[CH2:23][CH2:22][CH:21]1[C:31]1[CH:41]=[CH:40][C:34]([C:35](N(C)C)=[O:36])=[CH:33][CH:32]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]>C(O)C>[CH2:3]([S:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH:20]1[C:29]2[C:24](=[CH:25][C:26]([OH:30])=[CH:27][CH:28]=2)[CH2:23][CH2:22][CH:21]1[C:31]1[CH:41]=[CH:40][C:34]([C:35]([OH:1])=[O:36])=[CH:33][CH:32]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 20135542p-[(1RS,2RS)-1-(10-hexylthiodecyl)-6-hydroxy-1,2,3,4-tetrahydronaphth-2-yl]-N,N-dimethylbenzamide

Produkt 1

HCID 70400231p-[(1RS, 2RS)-1-(10-hexylthiodecyl)-6-hydroxy-1,2,3,4-tetrahydronaphth-2-yl]benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Aqueous 2N-sodium hydroxide solution (10 ml.) was added to a solution of p-[(1RS, 2RS)-1-(10-hexylthiodecyl)-6-hydroxy-1,2,3,4-tetrahydronaphth-2-yl]-N,N-dimethylbenzamide (Example 7; 0.24 g.) in ethanol (10 ml.) and the mixture was heated under reflux for 16 hours. The ethanol was removed by evaporation and the residue was acidified to pH 1 with aqueous 2N-hydrochloric acid and extracted three times with ethyl acetate (15 ml. each time). The combined extracts were washed with water, dried and evaporated to dryness and the residue was purified by chromatography on a silica gel column using a 4:1 v/v mixture of toluene and ethyl acetate as eluent. There was thus obtained as an oil p-[(1RS, 2RS)-1-(10-hexylthiodecyl)-6-hydroxy-1,2,3,4-tetrahydronaphth-2-yl]benzoic acid, the structure of which was confirmed by proton magnetic resonance and mass spectroscopy.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 16 hours
  3. customThe ethanol was removed by evaporation
  4. extractionextracted three times with ethyl acetate (15 ml
  5. washThe combined extracts were washed with water
  6. customdried
  7. customevaporated to dryness
  8. customthe residue was purified by chromatography on a silica gel column
  9. additiona 4:1 v/v mixture of toluene and ethyl acetate as eluent

Quellen und Nachweise

ORD-Eintrag
ord-1e273178f1b04420873368ab2d7cc733
Quelldatensatz
uspto-grants-1988_06
Patentnummer
US04751240

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