Hydrochloric Acid → HCID 54387966, compound

HRID 2254651Notes

Reaction equation

HRID 2254651 reaction equation
CC1(C)[O:6][C@@H:5]([CH2:7][O:8][S:9]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)(=[O:11])=[O:10])[CH2:4][O:3]1.Cl>CC(=O)C>[CH:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:20]=[CH:21][C:12]=1[S:9]([O:8][CH2:7][C@H:5]([OH:6])[CH2:4][OH:3])(=[O:10])=[O:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86747114HCID 86747114, compound

Product 1

HCID 54387966HCID 54387966, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 62 parts of (R)-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]2-naphthalenesulfonate, 400 parts of a hydrochloric acid solution 10% and 320 parts of 2-propanone was stirred for 2 hours at reflux temperature. After evaporation, the residue was taken up in trichloromethane. The organic layer was washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (98.2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 40 parts (73.7%) of (R)-(2,3-dihydroxypropyl) 2-naphthalenesulfonate as a residue (interm. 10).

Workup

  1. temperatureat reflux temperature
  2. customAfter evaporation
  3. washThe organic layer was washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (98.2 by volume) as eluent
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated

Sources & evidence

ORD record
ord-ff22eab2ce11438ba6e78182bf5b433a
Source dataset
uspto-grants-1993_08
Patent number
US05236944

Reaction notes

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