Water → 1-(4-Hydroxyphenylthio)-n-octadecane

HRID 1608546Notes

Reaction equation

HRID 1608546 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:15](Cl)[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][CH2:29][CH2:30][CH2:31][CH3:32].O>CN(C)C=O>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:32][CH2:31][CH2:30][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][CH3:15])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 188151-ChlorooctadecaneHCID 2401474-Mercaptophenol

Product 1

HCID 221790531-(4-Hydroxyphenylthio)-n-octadecaneYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Under a nitrogen atmosphere, p-hydroxythiophenol (126 g) was dissolved in N,N-dimethylformamide (600 ml) and thereto was added potassium carbonate (152 g). Thereto was added octadecyl chloride (318 g), followed by heating at 80° C. for 2 hours. After completion of the reaction, the reaction mixture was poured into water to precipitate a white solid. Thereto was added 5% hydrochloric acid to adjust the pH to acidic state and then, the white solid was filtered off under reduced pressure and then recrystallized from methyl ethyl ketone to obtain the desired product (261 g). Yield 70%; m.p. 95° C.

Workup

  1. customAfter completion of the reaction
  2. customto precipitate a white solid
  3. additionThereto was added 5% hydrochloric acid
  4. filtrationthe white solid was filtered off under reduced pressure
  5. customrecrystallized from methyl ethyl ketone

Sources & evidence

ORD record
ord-ba7ec9f547ea4cb48b338cd02e1cfa2b
Source dataset
uspto-grants-1995_03
Patent number
US05395815

Reaction notes

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