Sulfuric Acid → 2-(Aminomethyl)-4-tert-butylphenol hydrochloride
Reaktionsgleichung
[CH3:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[Cl:12]C[C:14]([NH:16]CO)=O.S(=O)(=O)(O)O>C(O)(=O)C.Cl.C(O)C.Cl>[ClH:12].[NH2:16][CH2:14][C:9]1[CH:10]=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[CH:6]=[CH:7][C:8]=1[OH:11]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 20 °C
Versuchsvorschrift
A mixture of 4-(1,1-dimethylethyl)phenol (75 g., 0.50 mole), 2-chloro-N-(hydroxymethyl)acetamide (61 g., 0.50 mole) and 96% sulfuric acid (50 ml.) in acetic acid (500 ml.) is stirred at 20° C. for 4 hours and then poured into ice water (2 l.) providing a heterogenous mixture. After decanting the aqueous solution, the insoluble white gum is extracted with ether. The organic extract is washed with water and saturated brine and evaporated in vacuo leaving a residual oil. A solution of the latter in 12N hydrochloric acid-ethanol (1:1; 400 ml.) is heated at reflux for 4 hours, diluted with 12N hydrochloric acid (200 ml.) and slowly cooled to -20° C. The deposited white crystalline solid is collected to provide pure 2-aminomethyl-4-(1,1-dimethylethyl)phenol hydrochloride (55 g.), m.p. 227°-229° C. (dec.).
Aufarbeitung
- customproviding a heterogenous mixture
- customAfter decanting the aqueous solution
- extractionthe insoluble white gum is extracted with ether
- extractionThe organic extract
- washis washed with water and saturated brine
- customevaporated in vacuo
- customleaving a residual oil
- temperatureat reflux for 4 hours
- temperatureslowly cooled to -20° C
- customThe deposited white crystalline solid is collected
Quellen und Nachweise
- ORD-Eintrag
- ord-751b6ec5a68448adbd50f3abe781b226
- Quelldatensatz
- uspto-grants-1977_06
- Patentnummer
- US04029816
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