Methanol → Methyl 2-(3-chlorophenyl)acetate

HRID 350436

Reaktionsgleichung

Reaktionsgleichung von HRID 350436
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH3:12]O.OS(O)(=O)=O>ClC(Cl)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 158793-Chlorophenylacetic acid

Produkt 1

HCID 2733544Methyl 2-(3-chlorophenyl)acetateAusbeute 107,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirred solution of 3-chlorophenylacetic acid (21.76 g, 127.6 mmol) in dichloroethane (100 ml) was added MeOH (15:6 ml, 383 mmol) and H2SO4 (1 ml) at room temperature. After 20 minutes stirring, the mixture was heated at 80° C. for 2 h. The reaction mixture was poured into ice water and extracted with CHCl3. The combined extracts were washed with aq. NaHCO3 and brine. After dried over Na2SO4, the extract was concentrated in vacuo to give methyl 3-chlorophenylacetate (25.4 g, 100%) as a colorless oil. 1H-NMR (CDCl3) δ 3.60 (s, 2H), 3.70 (s, 3H), 7.15–7.26 (m, 4H).

Aufarbeitung

  1. extractionextracted with CHCl3
  2. washThe combined extracts were washed with aq. NaHCO3 and brine
  3. dry with materialAfter dried over Na2SO4
  4. concentrationthe extract was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-58c61a5b79d44fc78fd27a8646da9633
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179819B2

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