Sulfuric Acid → (3-Iodo-2-methylphenyl)methanol

HRID 485538Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 485538
Cl.[OH:2][CH2:3][C:4]1[C:5]([CH3:11])=[C:6]([CH:8]=[CH:9][CH:10]=1)N.S(=O)(=O)(O)O.N([O-])=O.[Na+].[I-:21].[K+]>O.[Cu]>[I:21][C:6]1[C:5]([CH3:11])=[C:4]([CH:10]=[CH:9][CH:8]=1)[CH2:3][OH:2]

Komponenten

7

Edukt 4

HCID 1118Sulfuric Acid2×HCID 4875Potassium IodideHCID 20270659(3-Amino-2-methylphenyl)methanol hydrochlorideHCID 23668193Sodium Nitrite

Produkt 1

HCID 15035506(3-Iodo-2-methylphenyl)methanolAusbeute 24,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23978CopperKatalysatorHCID 962WaterLösungsmittel3×

Versuchsvorschrift

A stirred solution of 3-hydroxymethyl-2-methylaniline hydrochloride (43.4 g, 0.25 mole) and 17.2 ml of concentrated sulfuric acid in ice-water was cooled to 0°, and a solution of sodium nitrite (17.3 g, 0.25 mole) in water was added dropwise. Upon complete addition, the reaction mixture was stirred for an additional 0.5 hour, then an additional 8 ml of concentrated sulfuric acid was added dropwise. With the temperature maintained at 0°, a solution of potassium iodide (49.8 g, 0.30 mole) in water was added dropwise to the reaction mixture, followed by the addition of 0.1 gram of copper powder. The reaction mixture was slowly warmed to 70° where it stirred for 1 hour. The reaction mixture was then allowed to stand for 18 hours while cooling to room temperature. The reaction mixture was then taken up in water and extracted with chloroform. The chloroform extract was washed with an aqueous saturated solution of sodium bisulfite, then with water. The chloroform layer was dried and filtered. The filtrate was evaporated under reduced pressure to give 3-iodo-2-methylbenzyl alcohol (15.2 g) as a dark solid.

Aufarbeitung

  1. additionUpon complete addition
  2. temperatureWith the temperature maintained at 0°
  3. temperatureThe reaction mixture was slowly warmed to 70° where it
  4. stirringstirred for 1 hour
  5. waitto stand for 18 hours
  6. extractionextracted with chloroform
  7. extractionThe chloroform extract
  8. washwas washed with an aqueous saturated solution of sodium bisulfite
  9. dry with materialThe chloroform layer was dried
  10. filtrationfiltered
  11. customThe filtrate was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-57ad04b16b1348b88feed8f48d6b17c6
Quelldatensatz
uspto-grants-1985_08
Patentnummer
US04536591

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