Methylparaben → Methyl 4-((5-hydroxypentyl)oxy)benzoate

HRID 68641

Reaktionsgleichung

Reaktionsgleichung von HRID 68641
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:11])=[CH:9][CH:10]=1)=[O:4].[CH2:12](O)[CH2:13][CH2:14][CH2:15][CH2:16][OH:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.CCOC(/N=N/C(OCC)=O)=O>[OH:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 7456MethylparabenHCID 81051,5-PentanediolHCID 11776Triphenylphosphine

Produkt 1

HCID 65019122Methyl 4-((5-hydroxypentyl)oxy)benzoateAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 5462977Diethyl azodicarboxylateLösungsmittel

Versuchsvorschrift

To a solution of methyl p-hydroxybenzoate (3.38 g), 1,5-pentanediol (2.30 g) and triphenylphosphine (5.96 g) in tetrahydrofuran (100 mL), diethylazodicarboxylate (2.2N toluene solution, 10 mL) was slowly added under ice cooling. The reaction mixture was stirred under ice cooling for 16 hours. The reaction mixture was concentrated and the residue was washed with n-hexane-ethyl acetate solution (n-hexane:ethyl acetate=1:1). The reaction mixture was concentrated and then purified by silica gel chromatography (n-hexane:ethyl acetate=64:36→45:55) to obtain the title compound (3.58 g) having the following physical properties.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. washthe residue was washed with n-hexane-ethyl acetate solution (n-hexane:ethyl acetate=1:1)
  3. concentrationThe reaction mixture was concentrated
  4. custompurified by silica gel chromatography (n-hexane:ethyl acetate=64:36→45:55)

Quellen und Nachweise

ORD-Eintrag
ord-a3818d1f2e964e4abb49da749142a5ba
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822459B2

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