3,5-Dichloro-4-hydroxybenzoic acid → Benzenemethanol, 3,5-dichloro-4-hydroxy-

HRID 1063872

Reaktionsgleichung

Reaktionsgleichung von HRID 1063872
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:12])[C:10]=1[OH:11])[C:5](O)=[O:6].B.C1COCC1>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:8]=[C:9]([Cl:12])[C:10]=1[OH:11]

Komponenten

4

Edukt 2

HCID 187493,5-Dichloro-4-hydroxybenzoic acidHCID 2723981Borane;tetrahydrofuran

Produkt 1

HCID 176409Benzenemethanol, 3,5-dichloro-4-hydroxy-Ausbeute 99,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 3,5-dichloro-4-hydroxybenzoic acid (4.0 g, 19.3 mmol) in THF (60 ml) under argon was added borane-THF complex (39.0 mmol, 39.0 ml of 1 M solution in THF) dropwise. After addition, the reaction mixture was heated at 60° C. for 6 h, then quenched with water and extracted with ethyl acetate three times. The organic extract was washed with water, then brine, dried (sodium sulfate) and concentrated in vacuo to afford the title compound (3.7 g, 99%) as white solid. 1H NMR (400 MHz, CDCl3) δ 7.28 (s, 2H), 5.83 (s, 1H), 4.59 (s, 2H), MS: (M+1-H2O)=175

Aufarbeitung

  1. additionAfter addition
  2. customquenched with water
  3. extractionextracted with ethyl acetate three times
  4. extractionThe organic extract
  5. washwas washed with water
  6. dry with materialbrine, dried (sodium sulfate)
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cc32e226d4524a23a27f31ed755d1149
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06967220B2

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