Sodium Iodide → HCID 58079476, Verbindung

HRID 444998

Reaktionsgleichung

Reaktionsgleichung von HRID 444998
[C:1]([OH:20])(=[O:19])[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][C:16]([OH:18])=[O:17].C(NC(C)C)(C)C.[CH3:28][O:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34]Cl)=[CH:32][CH:31]=1.[Na+].[I-]>CN1C(=O)CCC1.O>[CH3:28][O:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][O:17][C:16](=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([OH:20])=[O:19])=[CH:32][CH:31]=1

Komponenten

7

Edukt 4

HCID 5238Sodium IodideHCID 7912DiisopropylamineHCID 10459Hexadecanedioic acidHCID 699934-Methyloxybenzyl chloride

Produkt 1

HCID 58079476HCID 58079476, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Hexadecandioic acid (2 g, 7 mmol) was dissolved in dry NMP (25 mL). Diisopropylamin (1.2 mL, 7 mmol) and 4-methoxybenzyl chloride (0.95 mL, 7 mmol) was added, followed by NaI (0.52 g, 3.5 mmol). The mixture was heated to 80° C. for 1 hour, poured into water (100 mL) and filtered. The precipate was washed with dichloromethane (150 mL), the dichoromethane phase was dried (Na2SO4) and solvent removed in vacuo to yield the crude product, which was recrystalized several times from heptane to yield hexadecanedioic acid mono-(4-methoxy-benzyl) ester.

Aufarbeitung

  1. filtrationfiltered
  2. washThe precipate was washed with dichloromethane (150 mL)
  3. dry with materialthe dichoromethane phase was dried (Na2SO4) and solvent
  4. customremoved in vacuo
  5. customto yield the crude product, which
  6. customwas recrystalized several times from heptane

Quellen und Nachweise

ORD-Eintrag
ord-d56b3bbfe0984fc58760dd7d3d47ace5
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476228B2

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