Hydrochloric Acid → 2,2-Bis{[(benzenesulfonyl)oxy]methyl}propane-1,3-diyl dibenzenesulfonate

HRID 1392377Notes

Reaction equation

HRID 1392377 reaction equation
[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][OH:5].[C:10]1([S:16](Cl)(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl>N1C=CC=CC=1>[C:10]1([S:16]([O:1][CH2:2][C:3]([CH2:8][O:9][S:16]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:18])=[O:17])([CH2:6][O:7][S:16]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:18])=[O:17])[CH2:4][O:5][S:16]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:18])=[O:17])(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7369Benzenesulfonyl chlorideHCID 8285Pentaerythritol

Product 1

HCID 2388742,2-Bis{[(benzenesulfonyl)oxy]methyl}propane-1,3-diyl dibenzenesulfonateYield 78%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
3 °C

Procedure

2.27 g (16.7 mmol) of pentaerythritol and 32.6 g of pyridine were placed in a 100 ml reaction vessel and 17.7 g (100 mmol) of benzenesulfonyl chloride was dropped over 0.7 hour while stirring at a temperature of 2 to 4° C. in a nitrogen atmosphere. After dropping, the temperature was raised to 15° C. and reaction was conducted for 4 hours. In a separate 300 ml reaction vessel, the reaction solution was dropped in an 11.3% by weight aqueous solution of hydrochloric acid while stirring at a temperature of 10 to 23° C. After dropping, the water phase was separated. The crystal precipitated by dissolving the oily matter by heating in 48 g of a mixed solution of acetone:methanol (weight ratio 3:1) and then concentrating was separated by filtration, washed and dried under reduced pressure to obtain 9.08 g of 2,2-bis(benzenesulfonyloxymethyl)-1,3-propanediol dibenzenesulfonate (yield: 78.0% [based on pentaerythritol]).

Workup

  1. additionwas dropped over 0.7 hour
  2. temperaturethe temperature was raised to 15° C.
  3. customreaction
  4. customIn a separate 300 ml reaction vessel
  5. stirringwhile stirring at a temperature of 10 to 23° C
  6. customthe water phase was separated
  7. customThe crystal precipitated
  8. dissolutionby dissolving the oily matter
  9. temperatureby heating in 48 g of a mixed solution of acetone
  10. concentrationmethanol (weight ratio 3:1) and then concentrating
  11. customwas separated by filtration
  12. washwashed
  13. customdried under reduced pressure

Sources & evidence

ORD record
ord-faba2a49c5af4fc1bca183154aa17e94
Source dataset
uspto-grants-2008_03
Patent number
US07342116B2

Reaction notes

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