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Decanal → Methyl-3-hydroxydodec-5-enoic acid

HRID 55740
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 55740
[CH:1](=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].COB(OC)OC.Br[CH2:20][C:21]([O:23][CH3:24])=[O:22].[NH4+].[OH-]>[Zn].OCC(CO)O.C1COCC1>[CH3:24][O:23][C:21](=[O:22])[CH2:20][CH:1]([OH:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 8175DecanalHCID 8470Trimethyl borateHCID 14923Ammonium HydroxideHCID 60984Methyl bromoacetate

Produkt 1

HCID 155752Methyl-3-hydroxydodec-5-enoic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysator
HCID 753
Glycerol
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

6.5 g of zinc, 15.5 g of decanal, 25 ml of trimethoxyborane, and 25 ml of dried THF were put into a 300 ml four-neck round-bottom flask, and 17.5 g of methyl bromoacetate was dripped at 20° C. for two hours in a nitrogen gas stream. After dripping, a resultant thereof was agitated at 20° C. for one hour, and thereafter, 25 ml of saturated ammonia aqueous solution and 25 ml of glycerin were added and agitated for ten minutes. An organic layer was separated and an aqueous solution layer was extracted two times by using diethyl ether. Thereafter, the organic solution was collected and subjected to desolvation. A residue thereof was purified by distillation to obtain a β-hydroxydodecanoic acid methyl ester.

Aufarbeitung

  1. stirringagitated for ten minutes
  2. customAn organic layer was separated
  3. extractionan aqueous solution layer was extracted two times
  4. customThereafter, the organic solution was collected
  5. distillationA residue thereof was purified by distillation

Quellen und Nachweise

ORD-Eintrag
ord-1c1b134520b04a6899a808cbee763b68
Quelldatensatz
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09433211B2

Notizen zur Reaktion

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