Hydrochloric Acid → 3-(3,4-Dichlorophenyl)-2-propene-1-ol acetate

HRID 481432

Reaktionsgleichung

Reaktionsgleichung von HRID 481432
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH2:11][OH:12])[CH:5]=[CH:6][C:7]=1[Cl:8].N1C=CC=CC=1.[CH3:19][C:20](Cl)=[O:21].Cl>ClCl.CN(C1C=CC=CN=1)C>[C:20]([O:12][CH2:11][CH:10]=[CH:9][C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)(=[O:21])[CH3:19]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6367Acetyl chlorideHCID 537091912-Propen-1-ol, 3-(3,4-dichlorophenyl)-

Produkt 1

HCID 538528443-(3,4-Dichlorophenyl)-2-propene-1-ol acetateAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 218852-DimethylaminopyridineKatalysatorHCID 24526ChlorineLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

Treat a solution of the product of step 2 (13.2 g, 65 mmol) in CH2 Cl2 (250 mL) at 0° C. with pyridine (7.89 mL, 97.5 mmol, 1.5 eq) and dimethylaminopyridine (397 mg, 3.25 0.05 eq), followed by CH3COCl (6.48 mL, 74.75 mmol, 1.15 eq). Allow the mixture to warm to 23° C., pour into 1M HCl (100 mL) and wash the resulting organic layer again with 1M HCl (100 mL), followed by water (5×100 mL; pH=6.5-7). Dry the organic layer (Na2SO4) and concentrate to obtain 15.4 g (62.9 mmol, 97%) of 3-(3,4-dichlorophenyl)-2-propene-1-ol acetate as a colorless oil.

Aufarbeitung

  1. washwash the resulting organic layer again with 1M HCl (100 mL)
  2. dry with materialDry the organic layer (Na2SO4)
  3. concentrationconcentrate

Quellen und Nachweise

ORD-Eintrag
ord-c6b90149cc644b18a385fbb3bcd67adf
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05789422

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