Potassium Hydroxide → 2-(Hydroxymethyl)-5-methylbenzoic acid

HRID 2361332

Reaktionsgleichung

Reaktionsgleichung von HRID 2361332
[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][O:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[OH-:12].[K+]>CO.O>[OH:12][CH2:6][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:10][C:9]=1[C:8]([OH:7])=[O:11]

Komponenten

5

Edukt 2

HCID 14797Potassium HydroxideHCID 6387566-Methylphthalide

Produkt 1

HCID 679628172-(Hydroxymethyl)-5-methylbenzoic acidAusbeute 59,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A colorless, homogeneous solution of 6-methylisobenzofuran-1(3H)-one (0.95 g, 6.41 mmol), KOH (0.576 g, 10.26 mmol) in methanol (20.52 mL) and water (5.13 mL) was refluxed. After two hr, the reaction was cooled to room temperature, concentrated in vacuo, and acidified with 1 M aqueous KHSO4 to pH ˜3. The mixture was extracted with EtOAc (4×50 mL). The combined extract was dried over MgSO4 and concentrated in vacuo to give the desired product (0.632 g, 3.81 mmol, 59.4% yield) as a white solid.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. extractionThe mixture was extracted with EtOAc (4×50 mL)
  3. extractionThe combined extract
  4. dry with materialwas dried over MgSO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8707a0efd23f4914ba4fe44be75131be
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08685969B2

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