Pentadecalactone → 1,15-Pentadecanediol

HRID 526290Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 526290
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1(=[O:23])[O:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1COCC1>[CH2:21]([OH:22])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][OH:23]

Komponenten

5

Edukt 3

HCID 235414PentadecalactoneHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 5189941,15-Pentadecanediol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Lithium aluminium hydride (1.52 g, 40.0 mmol, 2.0 eq.) was suspended in dry THF (80 mL) under an argon atmosphere. A solution of 15-pentadecanolide (4.80 g, 20.0 mmol) in dry THF (200 mL) was added at 0° C. Stirring was continued at this temperature for 1 h and for 3 more hours at r.t. Potassium sodium tartrate solution (20%, 50 mL) was added dropwise to the stirred reaction mixture. The phases were separated and the aqueous phase was extracted with diethyl ether (3×100 ml). The combined organic layers were dried over MgSO4. The solvent was removed in vacuo and the product was isolated as a white solid, which was used for the next step without purification. Yield: 4.68 g (96%).

Aufarbeitung

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with diethyl ether (3×100 ml)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. customThe solvent was removed in vacuo
  5. customthe product was isolated as a white solid, which
  6. customwas used for the next step without purification

Quellen und Nachweise

ORD-Eintrag
ord-d5db7491e832471b9c8214e13eeda5d5
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09345791B2

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