Benzyl Alcohol → Benzyl pent-4-ynoate

HRID 1377922Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1377922
[C:1]([OH:7])(=[O:6])[CH2:2][CH2:3][C:4]#[CH:5].C(Cl)(=O)C(Cl)=O.[CH2:14](O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>ClCCl.CN(C=O)C>[CH2:14]([O:6][C:1](=[O:7])[CH2:2][CH2:3][C:4]#[CH:5])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

6

Edukt 3

HCID 244Benzyl AlcoholHCID 224644-Pentynoic acidHCID 65578Oxalyl chloride

Produkt 1

HCID 561097Benzyl pent-4-ynoateAusbeute 134,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution in dichloromethane (25 mL) containing a few drops DMF of 4-pentynoic acid (2.49 g, 23.4 mmol) was added oxalyl chloride (2.2 mL, 25 mmol). The reaction mixture was stirred for 1.5 hours and benzyl alcohol (3.9 mL, 38 mmol) was added via syringe. The reaction mixture was stirred for 6 hours and then was extracted with saturated aqueous sodium carbonate. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo to give 4-pentynoic acid benzyl ester (5.94 g) as a yellow liquid.

Aufarbeitung

  1. stirringThe reaction mixture was stirred for 6 hours
  2. extractionwas extracted with saturated aqueous sodium carbonate
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7e3eb54c93f74cee80fa5b9de70512a9
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05665777

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