Ethylene Glycol → 2-(3-Chloropropyl)-2-thiophen-2-yl[1,3]dioxolane

HRID 1013118Notes

Reaction equation

HRID 1013118 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)=[O:6].[CH2:12](O)[CH2:13][OH:14]>C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]1([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)[O:14][CH2:13][CH2:12][O:6]1

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 1235114-Chloro-1-(2-thienyl)butan-1-one

Product 1

HCID 105375672-(3-Chloropropyl)-2-thiophen-2-yl[1,3]dioxolaneYield 97.3%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

Add 4-chloro-1-thiophen-2-yl-butan-1-one (10 g, 53 mmol), ethylene glycol (8.14 g, 131.2 mmol) and p-toluene sulfonic acid (362 mg, 1.6 mmol) to benzene (150 mL) and heat at reflux for 16 h under a water trap. Cool the reaction to RT and wash with 1 N NaOH solution (100 mL) and brine (150 mL). Dry (sodium sulfate) and concentrate to give the title product as a dark oil (12 g, 97%).

Workup

  1. temperatureheat
  2. temperatureat reflux for 16 h under a water trap
  3. temperatureCool
  4. customthe reaction to RT
  5. washwash with 1 N NaOH solution (100 mL) and brine (150 mL)
  6. dry with materialDry (sodium sulfate)
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-54e3857355a748f0a2255156f3d6139d
Source dataset
uspto-grants-2011_07
Patent number
US07981882B2

Reaction notes

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