Hydrochloric Acid → 2-Hydroxy-5-methylbenzyl alcohol

HRID 1739485

Reaktionsgleichung

Reaktionsgleichung von HRID 1739485
[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1.[CH3:12][C:13]1[CH:21]=[C:17]([C:18](O)=[O:19])[C:16]([OH:22])=[CH:15][CH:14]=1.Cl>O>[OH:19][CH2:18][C:17]1[CH:21]=[C:13]([CH3:12])[CH:14]=[CH:15][C:16]=1[OH:22]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 69735-Methylsalicylic acidHCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydride

Produkt 1

HCID 2574522-Hydroxy-5-methylbenzyl alcoholAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a suspension of LiAlH4 (2.5 g, 66 mmol) LiAlH4 in freshly distilled THF (8 ml) at 0° C. under argon, was added dropwise with stirring a solution of 5-methylsalicylic acid (5 g, 33 mmol) in freshly distilled THF (80 ml). Addition was complete in 0.75 hours and the reaction stirred at ambient temperature overnight. Careful addition of water (5 ml) was followed by the addition of ice (10 ml) and concentrated HCl (1 ml). The solvent was decanted and the residue treated with ethyl ether and ice water. The pH of the mixture was adjusted to pH 1 with concentrated HCl and the organic layer combined with the decanted solvent, washed with brine, dried (MgSO4) and evaporated. The residue was subjected to chromatography (eluant: ethyl ether/hexane) to give 2-hydroxymethyl-4-methylphenol as a white solid (3.1 g, 68%).

Aufarbeitung

  1. additionwas added dropwise
  2. additionAddition
  3. customThe solvent was decanted
  4. additionthe residue treated with ethyl ether and ice water
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-3c128d959a9f45278fa6e5f06b5f80f1
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05965741

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