Sodium borohydride → Tert-butyl 3-hydroxyoctadecanoate

HRID 236474Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 236474
[O:1]=[C:2]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:3][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[BH4-].[Na+]>CO>[OH:1][CH:2]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:3][C:4]([O:6][C:7]([CH3:8])([CH3:9])[CH3:10])=[O:5]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 16110963Tert-butyl 3-oxooctadecanoate

Produkt 1

HCID 13962663Tert-butyl 3-hydroxyoctadecanoateAusbeute 96,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of tert-butyl 3-oxooctadecanoate (130 g) in methanol (700 ml) was added sodium borohydride (15 g) at 0° C. in a portionwise. The mixture was stirred for 1 hour at 0° C. To the reaction mixture was added ice water and from this whole the object compound was extracted with ethyl acetate. The ethyl acetate solution was washed with water, dried over magnesium sulfate and then evaporated to give a residue which was dried up by using high vacuum pump to afford crude tert-butyl 3-hydroxyoctadecanoate (126.6 g) as an oil.

Aufarbeitung

  1. extractionfrom this whole the object compound was extracted with ethyl acetate
  2. washThe ethyl acetate solution was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customto give a residue which
  6. customwas dried up

Quellen und Nachweise

ORD-Eintrag
ord-cb6f234fc8bd413b9c61f0f659d9cb06
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04643990

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