Potassium Hydroxide → 4-(1-Hydroxyethyl)benzoic acid

HRID 1013520

Reaktionsgleichung

Reaktionsgleichung von HRID 1013520
C[O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:12])[CH3:11])=[CH:6][CH:5]=1.[OH-].[K+]>C1COCC1.CO.Cl>[OH:12][CH:10]([C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:13])=[O:2])=[CH:5][CH:6]=1)[CH3:11]

Komponenten

6

Edukt 2

HCID 14797Potassium HydroxideHCID 586417Methyl 4-(1-hydroxyethyl)benzoate

Produkt 1

HCID 5060614-(1-Hydroxyethyl)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of methyl-4-(1-hydroxyethyl)benzoate (2.00 g, 11.10 mmol) in a mixture of THF (20 mL) and MeOH (10 mL) was added 1 M KOH (13.32 mL, 13.32 mmol). After stirring at room temperature overnight, the solution was diluted with 2 N HCl and extracted with EtOAc (4×). The combined organic layers were dried (MgSO4) and evaporated to give 4-(1-hydroxyethyl)benzoic acid as a colorless solid. 1H NMR (DMSO-d6, 600 MHz) δ 7.86 (d, J=8.6 Hz, 2H), 7.43 (d, J=8.3 Hz, 2H), 4.75 (q, J=6.5 Hz, 1H), 1.30 (d, J=6.6 Hz, 3H). MS: cal'd 167 (MH+), exp 167 (MH+).

Aufarbeitung

  1. extractionextracted with EtOAc (4×)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-d55cee8dbb0c421dba668da42e56d3ea
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07981874B2

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