Dimethylformamide → HCID 117666794, compound

HRID 1753681Notes

Reaction equation

HRID 1753681 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.[CH3:15][O:16][CH2:17][CH2:18]Cl.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][CH2:18][CH2:17][O:16][CH3:15])=[CH:10][CH:9]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 123162-Chloroethyl methyl etherHCID 113101954-(phenylthio)phenol

Product 1

HCID 117666794HCID 117666794, compoundYield 101%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution was prepared by combining 10 g of 4-hydroxyphenyl phenyl sulfide which had been synthesized according to the well-known formulation, 5 g of 2-chloroethyl methyl ether, 7.4 g of potassium carbonate, and 20 g of DMF. The solution was aged at 80° C. for 16 hours. The aged solution was cooled to room temperature, to which 20 g of water was added to quench the reaction. To the solution, 40 g of toluene was added for extraction. The organic layer was separated and washed with sodium hydroxide aqueous solution and water in sequence. The organic layer was concentrated in vacuum, obtaining 13 g of the target compound, 4-(2-methoxyethoxy)phenyl phenyl sulfide as oily matter. Yield 93%.

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. concentrationThe organic layer was concentrated in vacuum

Sources & evidence

ORD record
ord-3115b032009d46d58441cf76189fdca9
Source dataset
uspto-grants-2015_10
Patent number
US09164384B2

Reaction notes

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