Sodium borohydride → 4-(Hydroxymethyl)-2-methylbenzoic acid

HRID 906084Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 906084
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([CH3:12])[CH:4]=1)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([CH3:12])[CH:4]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 207748714-Formyl-2-methylbenzoic acid

Produkt 1

HCID 232121724-(Hydroxymethyl)-2-methylbenzoic acidAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To 4-formyl-2-methylbenzoic acid (75 mg, 0.46 mmol), in methanol (5 ml), was added sodium borohydride (26 mg, 0.69 mmol). The solution was stirred at 25° C. for 1 h. The reaction was quenched with saturated aqueous ammonium chloride and the pH adjusted to 2 with 2 N aqueous hydrochloric acid, then extracted with dichloromethane. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting crude 4-(hydroxymethyl)-2-methylbenzoic acid (37 mg, 76%) was obtained and was used without further purification. 1H NMR (400 MHz, DMSO): 12.73-12.68 (s, 1H), 7.82-7.77 (d, 1H), 7.24-7.19 (m, 2H), 5.32-5.27 (m, 1H), 4.53-4.48 (d, 2H), 2.53-2.49 (s, 3H). MS (EI) for C9H10O3: 167 (MH+).

Aufarbeitung

  1. customThe reaction was quenched with saturated aqueous ammonium chloride
  2. extractionextracted with dichloromethane
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9a603f01e4b94270871c2d7e680f3030
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012956B2

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