Hydrochloric Acid → HCID 54216858, Verbindung

HRID 275178Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 275178
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:8]=[O:9])(=[O:3])[CH3:2].[BH4-].[Na+].Cl>CO>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:8][OH:9])(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 200905923-Acetoxy-4-pentyloxy-benzaldehyde

Produkt 1

HCID 54216858HCID 54216858, VerbindungAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

3-Acetoxy-4-pentyloxy-benzaldehyde (0.75 g., 3.0 mmol, 1 equiv.) is dissolved in 15 mL of MeOH, and the mixture cooled to 0° C. Sodium borohydride (0.230 g., 6 mmol., 2 equiv.) is added in portions. After stirring for 30 min., the mixture is neutralized with 1N HCl, and then extracted thrice with ether. The extracts are washed with brine, dried (MgSO4), and evaporated. Chromatography on silica gel using CH2Cl2 /hexane affords 3-acetoxy-4-pentyloxy-benzyl alcohol (12f) (0.680 g., 2.70 mmol., 90%): mp=35°-36° C.; 1H NMR (300 MHz, CDCl3) δ 7.17 (dd, J=2, 8 Hz, 1H, ArH), 7.05 (d, J=2 Hz, 1H, ArH), 6.92 (d, J=8 Hz, 1H, ArH), 4.85 (s, 1H, OH), 4.60 (s, 2H, ArCH2O), 3.95 (t, J=7 Hz, 2H, OCH2R), 2.30 (s, 3H, CH3CO), 1.75 (m, 2H, OCH2CH2), 1.38 (m, 4H, CH2CH2CH3), 0.90 (t, J=7 Hz, 3H, RCH2CH3).

Aufarbeitung

  1. extractionextracted thrice with ether
  2. washThe extracts are washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-aa3c10a639cf41c387fec4dcf678e762
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05391817

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