Potassium Hydroxide → HCID 59382257, Verbindung

HRID 41377Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 41377
[CH3:1][CH:2]([C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][C:16]=1[OH:17])[C:9]([O:11]CC)=[O:10])[C:3]([CH3:5])=[CH2:4].[OH-].[K+]>CO.O>[CH3:1][CH:2]([C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][C:16]=1[OH:17])[C:9]([OH:11])=[O:10])[C:3]([CH3:5])=[CH2:4]

Komponenten

5

Edukt 2

HCID 14797Potassium HydroxideHCID 59382270Ethyl 3-(1,2-dimethyl-allyl)-4-hydroxy-benzoate

Produkt 1

HCID 59382257HCID 59382257, VerbindungAusbeute 51,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

Ethyl 3-(1,2-dimethyl-allyl)-4-hydroxy-benzoate (600 mg, 2.56 mmol) was dissolved in methanol (20 ml), a solution of potassium hydroxide (560 mg, 10.0 mmol) in water (10 ml) was added and the mixture was stirred and held at reflux for 16 hours. Upon cooling the methanol was removed in vacuo and the solution acidified to pH 2 or below by the addition of 2M hydrochloric acid. The solution was extracted with dichloromethane, the organic layer was separated and the solvent was removed in vacuo to afford 3-(1,2-dimethyl-allyl)-4-hydroxy-benzoic acid (270 mg, 51%) as a colourless gum. 1H NMR (DMSO-d6) 12.38 (1H, br s), 10.22 (1H, br s), 7.63 (2H, m), 6.88 (1H, d), 4.90 (1H, s), 4.87 (1H, s), 3.75 (1H, q), 1.60 (3H, s), 1.28 (3H, d). MS: [M−H]+ 205.

Aufarbeitung

  1. temperatureat reflux for 16 hours
  2. customwas removed in vacuo
  3. additionthe solution acidified to pH 2 or below by the addition of 2M hydrochloric acid
  4. extractionThe solution was extracted with dichloromethane
  5. customthe organic layer was separated
  6. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-231ed56117774bd7a8ae50ec12db25b5
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530469B2

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