4-Hydroxybenzoic Acid → Benzoic acid, 4-hydroxy-, 2-methylbutyl ester

HRID 231009

Reaktionsgleichung

Reaktionsgleichung von HRID 231009
[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]([CH2:15][CH3:16])[CH2:13]O.S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[CH3:11][CH:12]([CH2:15][CH3:16])[CH2:13][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([OH:1])=[CH:3][CH:4]=1

Komponenten

5

Edukt 3

HCID 1354-Hydroxybenzoic AcidHCID 1118Sulfuric AcidHCID 2723602(S)-2-methyl-1-butanol

Produkt 1

HCID 13530949Benzoic acid, 4-hydroxy-, 2-methylbutyl esterAusbeute 88,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

0.29 mole(40.0 g) of 4-hydroxybenzoic acid and 0.35 mole(30.9 g) of (S)-(-)-2-methylbutanol were refluxed for 20 hours in 150 ml of toluene in the presence of 1 ml of conc. sulfuric acid. The reaction solution was concentrated, and then purified by column chromatography to obtain 53.2 g of 4-hydroxybenzoic acid 2-methylbutyl ester [[α]D23 =+4.95°(CHCl3)]. (yield: 88%)

Aufarbeitung

  1. concentrationThe reaction solution was concentrated
  2. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-469b52153c964ebba05ae7f9953356b8
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04844835

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