4-Hydroxybenzoic Acid → 3-Methylpentyl p-hydroxybenzoate

HRID 6317

Reaktionsgleichung

Reaktionsgleichung von HRID 6317
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[CH3:11][C@@H:12]([CH2:16][CH3:17])[CH2:13][CH2:14]O.S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:14][CH2:13][CH:12]([CH3:11])[CH2:16][CH3:17])=[O:7])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 1354-Hydroxybenzoic AcidHCID 1118Sulfuric AcidHCID 641003(S)-(+)-3-Methyl-1-pentanol

Produkt 1

HCID 190183233-Methylpentyl p-hydroxybenzoateAusbeute 80,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

13.7 g of p-hydroxybenzoic acid and 11.4 g of (S)-(+)-3-methyl-1-pentanol were refluxed for 10 hours in toluene in the presence of sulfuric acid, while removing out the generated water from the reaction system. Subsequently, the reaction solution was washed with water to remove the sulfuric acid out. The reaction solution was then dried, concentrated, and purified by column chromatography, to obtain 17.8 g of the objective ester compound (liquid state at room temperature ([α]D23 =+7.8° (CHCl3)). (Yield: 80%)

Aufarbeitung

  1. customwhile removing out the generated water from the reaction system
  2. washSubsequently, the reaction solution was washed with water
  3. customto remove the sulfuric acid out
  4. customThe reaction solution was then dried
  5. concentrationconcentrated
  6. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-9ad13e2b1c894f9687888c893b7a5b06
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05248446

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