Benzene → 2-(3-Thienyl)-1,3-dioxolane

HRID 2081757Notes

Reaction equation

HRID 2081757 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]=[O:7])=[CH:2]1.C1(C)C=CC(S(O)(=O)=[O:15])=CC=1.[CH:19]1[CH:24]=CC=CC=1>>[S:1]1[CH:5]=[CH:4][C:3]([CH:6]2[O:15][CH2:19][CH2:24][O:7]2)=[CH:2]1

Participants

4

Reactant 3

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 681353-Thiophenecarboxaldehyde

Product 1

HCID 3156302-(3-Thienyl)-1,3-dioxolaneYield 72%

Procedure

In a 100 mL roundbottom flask equipped with a dean stark trap and a reflux condenser, thiophene-3-carboxaldehyde and p-toluenesulfonic acid were dissolved in benzene (50 mL). The mixture was heated to reflux overnight. The reaction was cooled, washed with sat'd sodium bicarbonate, water, dried (MgSO4) and concentrated. Purification by fractional distillation (93°-95° C., 7.5 mm Hg) afforded 45.3 g (72%) of the desired dioxolane as a clear liquid.

Workup

  1. customIn a 100 mL roundbottom flask equipped with a dean stark trap and a reflux condenser
  2. temperatureThe mixture was heated
  3. temperatureto reflux overnight
  4. temperatureThe reaction was cooled
  5. washwashed with sat'd sodium bicarbonate, water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customPurification
  9. distillationby fractional distillation (93°-95° C., 7.5 mm Hg)

Sources & evidence

ORD record
ord-f16eb09f4e884bef94b79530b38c41c9
Source dataset
uspto-grants-1993_02
Patent number
US05185363

Reaction notes

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