4-Chlorosalicylic acid → 5-Chloro-2-(hydroxymethyl)phenol

HRID 514453

Reaktionsgleichung

Reaktionsgleichung von HRID 514453
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([OH:11])[CH:3]=1>C1COCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[C:4]([OH:11])[CH:3]=1

Komponenten

3

Edukt 1

HCID 787824-Chlorosalicylic acid

Produkt 1

HCID 3271485-Chloro-2-(hydroxymethyl)phenolAusbeute 63.058,699 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

BH3 (1M in THF, 359 mL) was added into a solution of 4-chloro-2-hydroxybenzoic acid (20.63 g, 0.12 mmol) in THF (40 mL) drop wise at 0° C. After which, the mixture was stirred at r.t. overnight. Extracted with EA twice, and washed the organic phase with brine and dried with anhydrous Na2SO4, concentrated to give the title compound (12 g, 63%). 1H NMR (400 MHz, DMSO-d6): δ 4.42 (2H, s), 4.97-5.06 (1H, m), 6.77 (1H, d, J=2.0 Hz), 6.82 (1H, dd, J=2.0 Hz, 8.0 Hz), 7.27 (1H, d, J=8.4 Hz), 9.85 (1H, s).

Aufarbeitung

  1. extractionExtracted with EA twice
  2. washwashed the organic phase with brine
  3. dry with materialdried with anhydrous Na2SO4
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-fb9b2566fa2442639839d8d0d4291d11
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09107916B2

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