Butyl isocyanate → 4-Chloro-4'-(N-butyl-carbamoyloxy)-alpha-ethyl-benzhydrol

HRID 1284928

Reaktionsgleichung

Reaktionsgleichung von HRID 1284928
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([CH2:15][CH3:16])([OH:14])[C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH2:19]([N:23]=[C:24]=[O:25])[CH2:20][CH2:21][CH3:22].C(N(CC)CC)C>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([CH2:15][CH3:16])([OH:14])[C:7]2[CH:12]=[CH:11][C:10]([O:13][C:24](=[O:25])[NH:23][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:9][CH:8]=2)=[CH:17][CH:18]=1

Komponenten

5

Edukt 3

HCID 8110Butyl isocyanateHCID 8471TriethylamineHCID 14727318alpha-Ethyl-alpha-(4-chlorophenyl)-4-hydroxy-benzylalcohol

Produkt 1

HCID 147273254-Chloro-4'-(N-butyl-carbamoyloxy)-alpha-ethyl-benzhydrol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

7.9 g. of 4-chloro-4'-hydroxy-α-ethyl-benzhydrol, 3.3 g. of n-butyl-isocyanate and 0.3 ml. of triethyl amine are dissolved in 40 ml. of dry tetrahydrofurane under stirring at 25° C., and the solution is allowed to stand at this temperature for 20 hours. When the reaction is complete, tetrahydrofurane is distilled off under reduced pressure, the residue is taken up in ether, the ethereal solution is shaken with a 5% aqueous sodium hydroxide solution and washed to neutral with water. The organic phase is dried over anhydrous magnesium sulfate, filtered and ether is distilled off in vacuo. Crystallization of the residue from a mixture of n-hexane and ethyl acetate yields 9.3 g. of the named compound, which melts at 78° to 79° C.

Aufarbeitung

  1. distillationtetrahydrofurane is distilled off under reduced pressure
  2. washwashed to neutral with water
  3. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. distillationether is distilled off in vacuo
  6. customCrystallization of the residue
  7. additionfrom a mixture of n-hexane and ethyl acetate
  8. customyields 9.3 g

Quellen und Nachweise

ORD-Eintrag
ord-3e65dc41c411420ea5bcad8682a8aae3
Quelldatensatz
uspto-grants-1986_01
Patentnummer
US04564630

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