Ethylene Glycol → HCID 14601399, compound

HRID 2352279Notes

Reaction equation

HRID 2352279 reaction equation
[S:1]1[C:5]([CH:6]=[O:7])=[CH:4][C:3]2[S:8][CH:9]=[CH:10][C:2]1=2.[CH2:11](O)[CH2:12][OH:13]>S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH+]1C=CC=CC=1.C1C=CC=CC=1>[O:7]1[CH2:11][CH2:12][O:13][CH:6]1[C:5]1[S:1][C:2]2[CH:10]=[CH:9][S:8][C:3]=2[CH:4]=1

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 737206Thieno(3,2-b)thiophene-2-carbaldehyde

Product 1

HCID 14601399HCID 14601399, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 241BenzeneSolvent

Procedure

A mixture of thieno[3,2-b]thiophene-2-carboxaldehyde (8) (23.30 g., 138.5 mmole); ethylene glycol (31 mL., 34.39 g., 554.0 mmole); pyridinium tosylate (2.5 g., 10 mmole); and benzene (200 mL) was stirred and refluxed and the water (3.2 mL) was removed by a Dean-Stark trap (~4 hours). The reaction was cooled to room temperature, extracted with water three times and then with a saturated solution of sodium bicarbonate. The organic layer was dried (MgSO4), filtered, and the solvent was evaporated to leave a crystalline mass. Trituration with a small amount of ether removed the color to give 24.72 g of a white crystalline product, mp. 88°-90° C. An additional 1.43 g of product was collected from the ether washing, mp 88°-89° C., yielding a total of 26.15 g of 2-(2-dioxolanyl)thieno[3,2-b]thiophene (9). This product was used in the next step without further purification.

Workup

  1. temperaturerefluxed
  2. customthe water (3.2 mL) was removed by a Dean-Stark trap (~4 hours)
  3. extractionextracted with water three times
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customto leave a crystalline mass
  8. customTrituration with a small amount of ether removed the color

Sources & evidence

ORD record
ord-ba584302b0704cae9276db5cc964c9fb
Source dataset
uspto-grants-1989_10
Patent number
US04876271

Reaction notes

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