4-Bromoanisole → 4-Methoxy-1-tetradecyl-benzene

HRID 235714

Reaktionsgleichung

Reaktionsgleichung von HRID 235714
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1.[CH2:11](Br)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>O1CCCC1>[CH3:10][O:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH3:11])=[CH:4][CH:5]=1

Komponenten

5

Edukt 3

HCID 77304-BromoanisoleHCID 8208Myristyl bromideHCID 5462224Magnesium

Produkt 1

HCID 202187144-Methoxy-1-tetradecyl-benzeneAusbeute 99,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

An about 3.70 g portion of magnesium was placed in a 100 ml, two-necked round bottom flask. The flask was flamed several times and about 28.5 g of p-bromoanisole and tetrahydrofuran were added. As soon as the reaction stopped it was refluxed for about 2 hours and then added to a boiling solution of about 21.07 g of tetradecyl bromide in tetrahydrofuran. Then about 9 ml of lithium cupric chloride was added and the mixture was refluxed for about 2 hours, then stirred at room temperature for about 16 hours, quenched with dilute hydrochloric acid, washed with ammonium chloride solution, sodium bicarbonate solution, brine and dried, giving about 23 g of the desired title compound, mp 38° C.

Aufarbeitung

  1. additionwere added
  2. temperaturewas refluxed for about 2 hours
  3. temperaturethe mixture was refluxed for about 2 hours
  4. customquenched with dilute hydrochloric acid
  5. washwashed with ammonium chloride solution, sodium bicarbonate solution, brine
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-1738770ce74c4b129a180eba2f6f6112
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04640913

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