Ethanol → 4-(1-Cyclohexen-1-yl)-3-ethylbenzoic acid

HRID 2189743Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2189743
[C:1]1([C:7]2[CH:14]=[CH:13]C(C#N)=[CH:9][C:8]=2[CH2:15][CH3:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[OH-:17].[K+].[CH2:19]([OH:21])[CH3:20]>O>[C:1]1([C:7]2[CH:14]=[CH:13][C:20]([C:19]([OH:17])=[O:21])=[CH:9][C:8]=2[CH2:15][CH3:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 593167164-(1-Cyclohexen-1-yl)-3-ethylbenzonitrile

Produkt 1

HCID 593168044-(1-Cyclohexen-1-yl)-3-ethylbenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

4-(1-Cyclohexen-1-yl)-3-ethylbenzonitrile (D11) (824 mg, 3.91 mmol) and potassium hydroxide (2.19 g, 39.1 mmol) in ethanol (36 mL) and water (8 mL) were heated at 90° C. (block temperature) for 20 h. The reaction mixture was concentrated in vacuo and the residue partitioned between ethyl acetate (120 mL) and aqueous hydrochloric acid (2M, 50 mL) before the organic phase was washed with further hydrochloric acid (2M, 50 mL), dried (phase separator) and concentrated in vacuo to give the title compound as a yellow oil (808 mg, 3.51 mmol). LCMS (ES): C15H18O2 requires 230; found 229 (M−H+).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue partitioned between ethyl acetate (120 mL) and aqueous hydrochloric acid (2M, 50 mL) before the organic phase
  3. washwas washed with further hydrochloric acid (2M, 50 mL)
  4. customdried (phase separator)
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8971d6fa0b3b488892e6344722a2b8f0
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324254B2

Notizen zur Reaktion

Wird geladen…