Triethylamine → 1-(Bromomethyl)-3-[[3-(hexadecyloxy)-2-methoxypropoxy]methyl]benzene

HRID 1586683

Reaktionsgleichung

Reaktionsgleichung von HRID 1586683
[CH2:1]([O:17][CH2:18][CH:19]([O:31][CH3:32])[CH2:20][O:21][CH2:22][C:23]1[CH:24]=[C:25]([CH2:29]O)[CH:26]=[CH:27][CH:28]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].S(Cl)(C)(=O)=O.C(N(CC)CC)C.[Br-:45].[Li+]>O1CCCC1.O>[Br:45][CH2:29][C:25]1[CH:26]=[CH:27][CH:28]=[C:23]([CH2:22][O:21][CH2:20][CH:19]([O:31][CH3:32])[CH2:18][O:17][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:24]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 82050Lithium BromideHCID 199395543-[[3-(Hexadecyloxy)-2-methoxypropoxy]methyl]benzenemethanol

Produkt 1

HCID 199395571-(Bromomethyl)-3-[[3-(hexadecyloxy)-2-methoxypropoxy]methyl]benzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 4 g of 3-[[3-(hexadecyloxy)-2-methoxypropoxy]methyl]benzenemethanol and 3.05 g of mesyl chloride in 40 ml of tetrahydrofuran at 0° C. was added over 20 minutes a solution of 2.69 g of triethylamine in 10 ml of tetrahydrofuran. A 7.71 g portion of lithium bromide was added and the mixture was stirred for 2 hours, diluted with water and filtered. The filtrate was poured into water and extracted with ether. The ether extract was washed with saturated sodium bicarbonate, dried and evaporated, giving 4.5 g of 1-(bromomethyl)-3-[[3-(hexadecyloxy)-2-methoxypropoxy]methyl]benzene as an oil.

Aufarbeitung

  1. filtrationfiltered
  2. additionThe filtrate was poured into water
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. washwas washed with saturated sodium bicarbonate
  6. customdried
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-e6eb8ba127ca466797457795961c8e63
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05215975

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