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

HRID 6314

Reaktionsgleichung

Reaktionsgleichung von HRID 6314
[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.O>C1(C)C=CC=CC=1>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:11][CH:12]([CH3:13])[CH2:15][CH3:16])=[O:7])=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 1354-Hydroxybenzoic AcidHCID 962WaterHCID 1118Sulfuric AcidHCID 2723602(S)-2-methyl-1-butanol

Produkt 1

HCID 13530949Benzoic acid, 4-hydroxy-, 2-methylbutyl esterAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

4.0 g of p-hydroxybenzoic acid and 12.5 g of (S)-(-)-2-methylbutanol were refluxed for 6 hours in toluene in the presence of sulfuric acid, while the generated water was removed out. Subsequently, the reaction solution was washed with water to remove sulfuric acid out. After the resulting solution was dried and concentrated, the concentrate was purified by column chromatography to obtain 5.0 g of the objective ester compound (liquid state at room temperature, [α]D23 =+4.9° (CHCl3)). (Yield: 83%)

Aufarbeitung

  1. customwas removed out
  2. washSubsequently, the reaction solution was washed with water
  3. customto remove sulfuric acid out
  4. customAfter the resulting solution was dried
  5. concentrationconcentrated
  6. customthe concentrate was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4871f52327694f1cbe2e0f27dd59dbfe
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05248446

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