Hydrochloric Acid → 4'-Hydroxy-n-heptadecananilide

HRID 1608541

Reaction equation

HRID 1608541 reaction equation
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([OH:8])[CH:2]=1.[C:9](Cl)(=[O:26])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].Cl>C(C(C)=O)C>[OH:8][C:3]1[CH:4]=[CH:5][C:6]([NH:7][C:9](=[O:26])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:1][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4034-AminophenolHCID 3516438Heptadecanoyl Chloride

Product 1

HCID 195970314'-Hydroxy-n-heptadecananilideYield 80%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
70 °C

Procedure

Under a nitrogen atmosphere, p-aminophenol (109 g) was suspended in methyl ethyl ketone (2000 ml) and the suspension was heated to 70° C. Heptadecanoyl chloride (152 g) was added to the suspension with vigorous stirring, followed by refluxing with heating for 2 hours. A 5% aqueous hydrochloric acid solution (500 ml) was added to the resulting reaction mixture with vigorous stirring. The reaction mixture was cooled to room temperature to precipitate a white crystal. This crystal was filtered off under reduced pressure and recrystallized from methyl ethyl ketone to obtain 150 g of the desired product. Yield 80%; m.p. 137° C.

Workup

  1. temperatureby refluxing
  2. temperaturewith heating for 2 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customto precipitate a white crystal
  5. filtrationThis crystal was filtered off under reduced pressure
  6. customrecrystallized from methyl ethyl ketone

Sources & evidence

ORD record
ord-5c0aa99bac964f92afe64b17ef855b9c
Source dataset
uspto-grants-1995_03
Patent number
US05395815

Linked notes

Loading…