Perchloric Acid → HCID 3707635, compound

HRID 1029983Notes

Reaction equation

HRID 1029983 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]1[O:21][CH:11]1[CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl(O)(=O)(=O)=[O:23]>O1CCCC1.O>[CH2:14]([O:13][CH2:12][CH:11]([OH:23])[CH:10]([OH:21])[CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 24247Perchloric AcidHCID 13255030(2R,3R)-2,3-Bis((benzyloxy)methyl)oxirane

Product 1

HCID 3707635HCID 3707635, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4.2 g of the 1,4-bis(benzyloxy)-2,3-epoxybutane thus obtained was dissolved in a mixture comprising 120 ml of tetrahydrofuran and 30 ml of water. Then 30 ml of an aqueous solution containing 6 ml of 60% perchloric acid was added dropwise thereto under ice-cooling and stirring. After stirring at the same temperature for additional 4 hours, the reaction mixture was poured into ice/water and extracted with ether. The extract was washed with water and dried. After distilling off the solvent, the obtained oily residue was purified by column chromatography (silica gel, hexane/ethyl acetate) to thereby give 2.7 g of 1,4-bis(benzyloxy)-2,3-butanediol as a colorless liquid.

Workup

  1. additionwas added dropwise
  2. temperatureunder ice-cooling
  3. stirringAfter stirring at the same temperature for additional 4 hours
  4. extractionextracted with ether
  5. washThe extract was washed with water
  6. customdried
  7. distillationAfter distilling off the solvent
  8. customthe obtained oily residue was purified by column chromatography (silica gel, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-4d74d5c5dc424b47b4f1e821508320fa
Source dataset
uspto-grants-1992_04
Patent number
US05102895

Reaction notes

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