4-Toluenesulfonyl chloride → HCID 11076628, compound

HRID 1753685Notes

Reaction equation

HRID 1753685 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.C1COCC1.[CH3:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][OH:24].[OH-].[Na+]>O>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:24][CH2:23][CH2:22][O:21][CH2:20][CH2:19][O:18][CH3:17])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8028Tetrahydrofuran2×HCID 8134Diethylene Glycol Monomethyl EtherHCID 14798Sodium Hydroxide

Product 1

HCID 11076628HCID 11076628, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under ice cooling, a mixture of 515 g of p-toluenesulfonyl chloride and 500 ml of THF was added dropwise to a mixture of 295 g of 2-(2-methoxyethoxy)ethanol, 589 g of 25 wt % NaOH aqueous solution, and 2,500 ml of THF. The reaction solution was aged for 1.5 hours, after which 1,500 ml of water was added to quench the reaction. The organic layer was separated and concentrated in vacuum. The concentrate was dissolved in a mixture of 660 ml toluene and 330 ml hexane, and washed with water. The organic layer was concentrated in vacuum, obtaining 684.74 g of the target compound, 2-(2-methoxyethoxy)ethyl p-toluenesulfonate as oily matter. Yield 97%.

Workup

  1. customto quench
  2. customthe reaction
  3. customThe organic layer was separated
  4. concentrationconcentrated in vacuum
  5. dissolutionThe concentrate was dissolved in a mixture of 660 ml toluene and 330 ml hexane
  6. washwashed with water
  7. concentrationThe organic layer was concentrated in vacuum

Sources & evidence

ORD record
ord-2036542604194db1a90de657546d519e
Source dataset
uspto-grants-2015_10
Patent number
US09164384B2

Reaction notes

Loading…