Benzyl mercaptan → 2-(6-Benzylthiohexyloxy)-5-methyl-1,3-benzenedicarboxaldehyde

HRID 22433

Reaktionsgleichung

Reaktionsgleichung von HRID 22433
[O-]CC.[Na+].Br[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[C:18]([CH:19]=[O:20])=[CH:17][C:16]([CH3:21])=[CH:15][C:14]=1[CH:22]=[O:23].[CH2:24]([SH:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(O)C>[CH2:24]([S:31][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[C:18]([CH:19]=[O:20])=[CH:17][C:16]([CH3:21])=[CH:15][C:14]=1[CH:22]=[O:23])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Komponenten

5

Edukt 3

HCID 7509Benzyl mercaptanHCID 2723922Sodium ethoxideHCID 199302642-(6-Bromohexyloxy)-5-methyl-1,3-benzenedicarboxaldehyde

Produkt 1

HCID 199302892-(6-Benzylthiohexyloxy)-5-methyl-1,3-benzenedicarboxaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of sodium ethoxide (69 mg sodium, 3 mmol in ethanol 1 ml) was added to a stirred suspension of 2-(6-bromohexyloxy)-5-methyl-1,3-benzenedicarboxaldehyde (0.98 g, 3 mmol) and benzyl mercaptan (0.35 g, 3 mmol) in ethanol (10 ml) at room temperature under nitrogen. After 1 hour evaporated, water (10 ml) and 2M sodium hydroxide (2 ml) added and extracted with diethyl ether (10 ml). The extracts were washed with water, dried, filtered and evaporated to an oil (1.12 g). Chromatography on silica eluting with dichloromethane gave 2-(6-benzylthiohexyloxy)-5-methyl-1,3-benzenedicarboxaldehyde as a colourless oil.

Aufarbeitung

  1. customAfter 1 hour evaporated
  2. additionwater (10 ml) and 2M sodium hydroxide (2 ml) added
  3. extractionextracted with diethyl ether (10 ml)
  4. washThe extracts were washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated to an oil (1.12 g)

Quellen und Nachweise

ORD-Eintrag
ord-7f6483fff6624318bcdbcd4153c44add
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05428065

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