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Benzoic acid, 2,3-dichloro-, methyl ester → (2,3-Dichlorophenyl)methanol

HRID 510431
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 510431
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:9]=1[C:10](OC)=[O:11]>C1COCC1>[Cl:7][C:8]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:9]=1[CH2:10][OH:11]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 76189Benzoic acid, 2,3-dichloro-, methyl esterHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 228603(2,3-Dichlorophenyl)methanolAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A suspension of LiAlH4 (7.4 g, 0.195 mol) in THF (500 mL) was stirred at 0° C. A solution of methyl 2,3-dichlorobenzoate (49 g, 0.244 mol) in THF (50 mL) was added dropwise into the above mixture at 0-5° C. Then the mixture was stirred at room temperature for 2 h. The reaction mixture was quenched with ethyl acetate (15 mL), water (7.5 mL), 15% NaOH (7.5 mL) and water (22.5 mL), filtered and the filtrate was concentrated. The resulting residue was dissolved with DCM (500 mL) and washed with brine. The organic layer was dried over Na2SO4, filtered and the filtrate was concentrated to provide the titled compound (37 g, 88%), as a white solid; 1H NMR (300 MHz, CDCl3) δ ppm 4.81 (d, J=6.3 Hz, 2H), 7.24 (t, J=7.8 Hz, 1H), 7.42-7.45 (m, 2H).

Aufarbeitung

  1. stirringThen the mixture was stirred at room temperature for 2 h
  2. customThe reaction mixture was quenched with ethyl acetate (15 mL), water (7.5 mL), 15% NaOH (7.5 mL) and water (22.5 mL)
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe resulting residue was dissolved with DCM (500 mL)
  6. washwashed with brine
  7. dry with materialThe organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-06ed947d354945b5b89204d859be8b30
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09096605B2

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