Dimethylformamide → HCID 117666823, compound

HRID 1753677Notes

Reaction equation

HRID 1753677 reaction equation
[C:1]1([S:7][C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>C1(C)C=CC=CC=1.O>[C:1]1([S:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:10][CH:9]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 81011-BromohexaneHCID 11430Potassium CarbonateHCID 113101954-(phenylthio)phenol

Product 1

HCID 117666823HCID 117666823, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution was prepared by combining 15 g of (4-hydroxyphenyl) phenyl sulfide which had been synthesized according to the well-known formulation, 11 g of 1-bromohexane, 9 g of potassium carbonate, and 30 g of DMF. The solution was aged at 80° C. for 16 hours. The aged solution was cooled to room temperature, to which 30 g of water was added to quench the reaction. To the solution, 50 g of toluene was added for extraction. The organic layer was separated and washed with sodium hydroxide aqueous solution and water in sequence. On subsequent concentration in vacuum, 16 g of the target compound, (4-hexyloxyphenyl) phenyl sulfide was obtained as oily matter. Yield 90%.

Workup

  1. customA solution was prepared
  2. customhad been synthesized
  3. additionwas added
  4. customto quench
  5. customthe reaction
  6. customThe organic layer was separated
  7. washwashed with sodium hydroxide aqueous solution and water in sequence
  8. concentrationOn subsequent concentration in vacuum, 16 g of the target compound

Sources & evidence

ORD record
ord-88a342cc91cc40d68d522657fb1c9b58
Source dataset
uspto-grants-2015_10
Patent number
US09164384B2

Reaction notes

Loading…