Hydrochloric Acid → 3-Phenylbutyric acid

HRID 593262

Reaktionsgleichung

Reaktionsgleichung von HRID 593262
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:13]([OH:18])(=[O:17])/[CH:14]=[CH:15]/[CH3:16].Cl>O1CCCC1>[C:7]1([CH:15]([CH3:16])[CH2:14][C:13]([OH:18])=[O:17])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 7961BromobenzeneHCID 637090Crotonic AcidHCID 178418339Butyllithium

Produkt 1

HCID 207243-Phenylbutyric acidAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

As presented in the following reaction formula, n-butyllithium (n-BuLi; 428 mL, 1.07 mol) was added dropwise at −78° C. to −65° C. to a mixture of bromobenzene (166 g, 1.07 mol) in tetrahydrofuran (THF; 500 mL), followed by stirring at −78° C. for 0.5 hours. Then, (E)-but-2-enoic acid (46 g, 0.53 mol) was added dropwise to the resulting mixture. After the completion of reaction, the mixture was treated with hydrochloric acid so that the pH thereof was adjusted to 1.0, and then extracted twice with 500 mL of dichloromethane (DCM). The combined organic phase was dried and concentrated with magnesium sulfate to give a crude product, which was purified by column chromatography (using 300 g of silica gel (product of Merck Co., Ltd.) to give 3-phenylbutanoic acid (52 g, yield: 60%) as a yellow liquid.

Aufarbeitung

  1. customAfter the completion of reaction
  2. extractionextracted twice with 500 mL of dichloromethane (DCM)
  3. customThe combined organic phase was dried
  4. concentrationconcentrated with magnesium sulfate
  5. customto give a crude product, which
  6. customwas purified by column chromatography (

Quellen und Nachweise

ORD-Eintrag
ord-d6fb234995ba403ea1a361ffbcd8273f
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242928B2

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