Hydrochloric Acid → 4-(Hexadecylamino)benzoic acid

HRID 1659628Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1659628
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[OH-].[K+].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].[Cl-].C([P+](CCCC)(CCCC)CCCC)CCCCCCCCCCCCCCC.Cl>C(O)C>[CH2:29]([NH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 9784-Aminobenzoic AcidHCID 82131-BromohexadecaneHCID 14797Potassium HydroxideHCID 9890573Phosphonium, tributylhexadecyl-, chloride

Produkt 1

HCID 472634-(Hexadecylamino)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

27.4 g (0.2 mol) of 4-aminobenzoic acid, 11.2 g of KOH, 64 g (0.21 mol) of 1-bromohexadecane and 4.64 g (10 mmol) of hexadecyltributylphosphonium chloride were suspended in 250 ml of ethanol (96%) and the reaction mixture was stirred for 12 hours at reflux temperature. While the solution was still hot, there were added, drop by drop, 80 ml of conc. HCl and the reaction mixture was left to cool down to ambient temperature. Thereupon the precipitated product was separated on a suction filter, washed with water and dried. After the crystallization of the crude product from benzene, there was obtained the 4-(n-hexadecylamino)-benzoic acid, m.p. 107°-107° C., complete m.p. 122°-126° C., which could be optionally converted into its sodium salt.

Aufarbeitung

  1. temperatureat reflux temperature
  2. additionthere were added
  3. customThereupon the precipitated product was separated on a suction
  4. filtrationfilter
  5. washwashed with water
  6. customdried
  7. customAfter the crystallization of the crude product from benzene

Quellen und Nachweise

ORD-Eintrag
ord-753192602afc4e6bbffd5580619d74ca
Quelldatensatz
uspto-grants-1981_12
Patentnummer
US04304929

Notizen zur Reaktion

Wird geladen…