Ethylene Glycol → 2-(4-Trifluoromethylsulfonyloxy naphthyl)dioxolane

HRID 1166741Notes

Reaction equation

HRID 1166741 reaction equation
[F:1][C:2]([F:20])([F:19])[S:3]([O:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]=[O:18])=[CH:9][CH:8]=1)(=[O:5])=[O:4].[CH2:21](O)[CH2:22][OH:23].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:20][C:2]([F:19])([F:1])[S:3]([O:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]2[O:23][CH2:22][CH2:21][O:18]2)=[CH:9][CH:8]=1)(=[O:4])=[O:5]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 109903314-Formyl-1-naphthyl trifluoromethanesulfonate

Product 1

HCID 540831252-(4-Trifluoromethylsulfonyloxy naphthyl)dioxolane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-trifluoromethylsulfonyloxy naphthaldehyde (4.09 g, 13.4 mmol), ethylene glycol (1.5 mL, 1.67 g, 26.9 mmol), and p-toluene sulfonic acid (250 mg) in toluene (250 mL) was refluxed for 16 hr using a Dean-Stark trap. The solution was allowed to reach room temperature, was washed with satd. NaHCO3-sol. (2×80 mL), brine (80 mL), dried (MgSO4), and concentrated to give a yellow oil (4.79 g, quant).

Workup

  1. customto reach room temperature
  2. washwas washed with satd
  3. dry with material(2×80 mL), brine (80 mL), dried (MgSO4)
  4. concentrationconcentrated
  5. customto give a yellow oil (4.79 g, quant)

Sources & evidence

ORD record
ord-2296a66f602a40fe87d58330c450f928
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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