Water → HCID 22753009, compound

HRID 2163278Notes

Reaction equation

HRID 2163278 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5](O)=[CH:4][C:3]=1[NH:10][C:11]([CH3:13])=[O:12].[CH2:14](Br)[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].O>[OH-].[K+].C(O)C>[C:11]([NH:10][C:3]1[CH:4]=[C:5]([CH2:29][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])[C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1])(=[O:12])[CH3:13]

Participants

6

Reactant 3

HCID 962WaterHCID 82131-BromohexadecaneHCID 2735988N-(2,4-Dichloro-5-hydroxyphenyl)acetamide

Product 1

HCID 22753009HCID 22753009, compoundYield 74.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14797Potassium HydroxideSolvent

Conditions

Temperature
25 °C

Procedure

In a solution of 5.6 g of potassium hydroxide in 200 ml of ethanol was dissolved 22 g of 4,6-dichloro-3-acetaminophenol (which was synthesized using the method described in Beilstein, 13, I, 135). To the solution was added 30.5 g of hexadecyl bromide. After the mixture was stirred for an hour at room temperature (about 20-30° C.), the mixture was heated at reflux for 8 hours. The reaction mixture was poured into water. The resulting precipitate was recovered by filtration and washed with methanol to obtain 32 g of the desired product. The melting point thereof was 92 to 93.5° C.

Workup

  1. customwas synthesized
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 8 hours
  4. filtrationThe resulting precipitate was recovered by filtration
  5. washwashed with methanol

Sources & evidence

ORD record
ord-3b840c488f5449359c83fb68d3ee5019
Source dataset
uspto-grants-1979_01
Patent number
US04133686

Reaction notes

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