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Hydrochloric Acid → 1-(Hexadecyloxy)but-3-EN-2-OL

HRID 255963
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 255963
[Mg].[CH:2](Br)=[CH2:3].[CH2:5]([O:21][CH2:22][CH:23]=[O:24])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].Cl>O1CCCC1.BrC(Br)C.CCOCC>[CH2:5]([O:21][CH2:22][CH:23]([OH:24])[CH:2]=[CH2:3])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 11641BromoetheneHCID 5462224Magnesium2×HCID 14785848(Hexadecyloxy) acetaldehyde

Produkt 1

HCID 139590711-(Hexadecyloxy)but-3-EN-2-OLAusbeute 41,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11201
1,1-Dibromoethane
Katalysator
HCID 3283Diethyl EtherLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirring mixture of 5.67 g of magnesium in 25 ml of tetrahydrofuran was added 10 drops of dibromoethane as an initiator. After the reaction began another 100 ml of tetrahydrofuran was added followed by the dropwise addition of a solution of 49.85 g of vinyl bromide in 250 ml of tetrahydrofuran at a rate to maintain reflux. After all of the magnesium had reacted, the solution was cooled to 0° C. and a solution of 44.2 g of (hexadecyloxy) acetaldehyde, prepared by the procedure of Example 3, in 175 ml of ether was added dropwise over 1/2 hour. After 1 hour at room temperature dilute hydrochloric acid was added. The tetrahydrofuran was removed and the residue was extracted with ether. The ether layer was washed with brine, dried and the solvent removed. The residue was purified by HPLC [hexane: ether (9:1), two columns, two passes] giving an oil which was distilled via a Kugelrohr apparatus (185°-190° C., 0.2 mm) giving a colorles oil which solidified on standing to give 20.17 g of the desired compound.

Aufarbeitung

  1. additionwas added
  2. temperatureto maintain
  3. temperaturereflux
  4. additionwas added dropwise over 1/2 hour
  5. customThe tetrahydrofuran was removed
  6. extractionthe residue was extracted with ether
  7. washThe ether layer was washed with brine
  8. customdried
  9. customthe solvent removed
  10. customThe residue was purified by HPLC [hexane: ether (9:1), two columns, two passes]
  11. customgiving an oil which
  12. distillationwas distilled via a Kugelrohr apparatus (185°-190° C., 0.2 mm)
  13. customgiving a colorles oil which

Quellen und Nachweise

ORD-Eintrag
ord-41414b2cf6584599ac72779c5a79dd96
Quelldatensatz
uspto-grants-1987_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04699990

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