Benzyl Bromide → Benzyl 3-hydroxytetradecanoate

HRID 24982Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 24982
[OH:1][CH:2]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:3][C:4]([OH:6])=[O:5].C(N(CC)CC)C.[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C>[OH:1][CH:2]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:3][C:4]([O:6][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:5]

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 16064(+-)-3-Hydroxytetradecanoic acid

Produkt 1

HCID 10520747Benzyl 3-hydroxytetradecanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 3-hydroxymyristic acid (5.00 g) and triethylamine (2.85 g) in DMF (50 ml) was added benzyl bromide (2.43 ml) and the mixture was stirred at room temperature overnight. After the solvent was removed in vacuo, to the residue were added ethyl acetate and water. The separated ethyl acetate layer was washed twice with water and then dried over anhydrous sodium sulfate. After the ethyl acetate was removed in vacuo, purification was carried out by a silica gel column chromatography (silica gel 30 g, chloroform:methanol=100:0-10) to afford 3.69 g of benzyl 3-hydroxymyristate.

Aufarbeitung

  1. customAfter the solvent was removed in vacuo, to the residue
  2. additionwere added ethyl acetate and water
  3. washThe separated ethyl acetate layer was washed twice with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter the ethyl acetate was removed in vacuo, purification

Quellen und Nachweise

ORD-Eintrag
ord-e8fb2a66ea7c487f8f69063cb844a64a
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858585B1

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