Hydrochloric Acid → 1-(4-Chlorophenyl)-2-cyclopropylethanol

HRID 1074320Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1074320
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:12])[CH2:9][CH:10]=[CH2:11])=[CH:4][CH:3]=1.Br[CH2:14]Br.Cl>CCOCC.[Zn].[Cu]Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:12])[CH2:9][CH:10]2[CH2:14][CH2:11]2)=[CH:6][CH:7]=1

Komponenten

7

Edukt 3

HCID 313Hydrochloric AcidHCID 3024DibromomethaneHCID 27577711-(4-Chlorophenyl)-3-buten-1-ol

Produkt 1

HCID 190783841-(4-Chlorophenyl)-2-cyclopropylethanolAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 62652Cuprous chlorideKatalysatorHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Crude 4-(4-chlorophenyl)but-1-en-4-ol from the previous reaction (85.37 g, approximately 92% pure, approximately 430 mmol), zinc dust (121.5 g, 1.86 mol), copper(I) chloride (18.69 g, 187 mmol) and dibromomethane (163.6 g, 936 mmol) in dry ether (250 ml) were heated under reflux for 3 hours in a sonic bath and then poured into 2M hydrochloric acid. The mixture was extracted with ether and the extract washed with 2M hydrochloric acid and brine, dried and evaporated in vacuo. Chromatography [SiO2, hexane-ethyl acetate (90:10)] gave 1-(4-chlorophenyl)-2-cyclopropylethanol (37.24 g, 44% from 4-chlorobenzaldehyde).

Aufarbeitung

  1. temperaturewere heated
  2. temperatureunder reflux for 3 hours in a sonic bath
  3. extractionThe mixture was extracted with ether
  4. washthe extract washed with 2M hydrochloric acid and brine
  5. customdried
  6. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5bcafa100fe04ffda690b6f9b6c612b9
Quelldatensatz
uspto-grants-1990_11
Patentnummer
US04973767

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