2-Butoxyethanol → HCID 88123833, compound

HRID 1779915Notes

Reaction equation

HRID 1779915 reaction equation
[CH2:1]([O:5][CH2:6][CH2:7][OH:8])[CH2:2][CH2:3][CH3:4].[C:9]1([CH3:19])[C:10]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:12]=[CH:13][CH:14]=1>N1C=CC=CC=1>[C:9]1([CH3:19])[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([O:8][CH2:7][CH2:6][O:5][CH2:1][CH2:2][CH2:3][CH3:4])(=[O:17])=[O:16]

Participants

4

Reactant 2

HCID 81332-ButoxyethanolHCID 8623o-Toluenesulfonyl chloride

Product 1

HCID 88123833HCID 88123833, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a cold (0° C.) solution of 118.18 (1 mol) of 2-butoxy-ethanol in anhydrous pyridine, was added 190.66 g (1 mol) of toluenesulfonylchloride. The resultant reaction mixture was allowed to react for approximately one hour at 0° C., then at room temperature for approximately two hours. When the reaction was substantially complete, as indicated by TLC, the reaction mixture was concentrated in vacuo to provide a residue. This residue was partitioned between diethyl ether and a 1N aqueous hydrochloric acid solution and the organic phase was washed sequentially with a 2N sodium hydroxide solution, a 1N hydrochloric acid solution, water, and brine, and then dried over sodium sulfate, filtered and concentrated in vacuo to provide 200.39 g of a light gold oil.

Workup

  1. customThe resultant reaction mixture
  2. customto react for approximately one hour at 0° C.
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. customto provide a residue
  5. customThis residue was partitioned between diethyl ether
  6. washa 1N aqueous hydrochloric acid solution and the organic phase was washed sequentially with a 2N sodium hydroxide solution
  7. dry with materiala 1N hydrochloric acid solution, water, and brine, and then dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d2cff705ffdc4789ad857a8ad0293def
Source dataset
uspto-grants-1997_05
Patent number
US05629290

Reaction notes

Loading…