1,4-Butanediol → HCID 53643992, compound

HRID 1709755Notes

Reaction equation

HRID 1709755 reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][CH2:4][OH:5].[CH:7]([S:13](Cl)(=[O:15])=[O:14])([S:9](Cl)(=[O:11])=[O:10])[CH3:8].C(N(CC)CC)C.[Cl-].[Cl-].[Ca+2]>C(COC)OC>[CH:7]1([S:13](=[O:15])(=[O:14])[O:6][CH2:1][CH2:2][CH2:3][CH2:4][O:5][S:9]1(=[O:11])=[O:10])[CH3:8]

Participants

6

Reactant 4

HCID 80641,4-ButanediolHCID 8471TriethylamineHCID 5284359Calcium ChlorideHCID 230367261,1-Ethanedisulfonyl chloride

Product 1

HCID 53643992HCID 53643992, compoundYield 9.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Procedure

1,4-Butanediol, obtained from Aldrich Chemical Co. (3.6 g, 0.04 mole) was dissolved in 75 ml of glyme in a 1 liter round bottom flask. A solution of 1,1-ethanedisulfonyl chloride (9.1 g, 0.04 mole) dissolved in 25 ml of glyme wa added to the flask through a dropping funnel. The reaction mixture was kept below -20° C. with a dowanol-dry ice bath. Triethylamine (8.08 g, 0.08 mole) dissolved in 100 ml of glyme was added to the mixture through a 125 ml dropping funnel over a period of 1 hour. Care was taken to maintain anhydrous conditions by covering the dropping funnels with drying tubes containing CaCl2. The reaction mixture was brought to 25° C. in a cold water bath. The glyme was removed by roto-evaporation, at a temperature below 37° C. The oily yellow residue that remained after removal of the glyme was washed once with 100 ml of 5% sodium bicarbonate and once with 50 ml of cold distilled water, the resulting emulsion being centrifuged immediately to separate the product, and aqueous material decanted. The remaining precipitate was dried under vacuum. The white, powdery solid which remained weighed 0.90 g, representing a 9.2% yield. Product identification was confirmed by characteristic IR and proton NMR spectral features. The product decomposed between 115 and 138° C. The product was soluble to less than about 0.01 gram in 1 ml of either methylene chloride or acetonitrile.

Workup

  1. additionwa added to the flask through a dropping funnel
  2. customThe reaction mixture was kept below -20° C. with a dowanol-dry ice bath
  3. additionwas added to the mixture through a 125 ml
  4. customof 1 hour
  5. temperatureto maintain anhydrous conditions
  6. customThe reaction mixture was brought to 25° C. in a cold water bath
  7. customThe glyme was removed by roto-evaporation, at a temperature below 37° C
  8. customafter removal of the glyme
  9. washwas washed once with 100 ml of 5% sodium bicarbonate and once with 50 ml
  10. distillationof cold distilled water
  11. customto separate the product, and aqueous material
  12. customdecanted
  13. customThe remaining precipitate was dried under vacuum
  14. customdecomposed between 115 and 138° C

Sources & evidence

ORD record
ord-b8548ffa984b434baf74a50e065ef1ce
Source dataset
uspto-grants-1990_08
Patent number
US04950768

Reaction notes

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