4-Toluenesulfonyl chloride → HCID 11015881, compound

HRID 929160Notes

Reaction equation

HRID 929160 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH2:12]1[O:16][C@@H:15]2[C@@H:17]([OH:20])[CH2:18][O:19][C@@H:14]2[C@@H:13]1[OH:21]>N1C=CC=CC=1>[CH3:11][C:1]1[CH:6]=[CH:5][C:4]([S:7]([O:21][C@@H:13]2[CH2:12][O:16][C@@H:15]3[C@@H:17]([O:20][S:7]([C:4]4[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=4)(=[O:9])=[O:8])[CH2:18][O:19][C@H:14]23)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 12597Isosorbide

Product 1

HCID 11015881HCID 11015881, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

p-Toluenesulfonyl chloride (2722 g, 14.28 mol) was added to a solution of isosorbide (869 g, 5.95 mol) in pyridine (5000 mL) in portions with stirring at 0° C. After the reaction mixture was stirred at ambient temperature overnight, the mixture was poured into ice-water (5000 mL) with stirring, and extracted with DCM (4000 mL×3). The combined organic layers were washed successively with water (3000 mL×3), 1 N aqueous HCl (3000 mL×3, pH=6), and saturated aqueous NaHCO3 (3000 mL×2), and dried over anhydrous Na2SO4. After removal of the solvent via vacuum, ethanol (1000 mL) was added. The resulting precipitate was filtered, and washed with ethanol to give the desired product as a white solid.

Workup

  1. stirringAfter the reaction mixture was stirred at ambient temperature overnight
  2. stirringwith stirring
  3. extractionextracted with DCM (4000 mL×3)
  4. washThe combined organic layers were washed successively with water (3000 mL×3), 1 N aqueous HCl (3000 mL×3, pH=6), and saturated aqueous NaHCO3 (3000 mL×2)
  5. dry with materialdried over anhydrous Na2SO4
  6. customAfter removal of the solvent via vacuum, ethanol (1000 mL)
  7. additionwas added
  8. filtrationThe resulting precipitate was filtered
  9. washwashed with ethanol

Sources & evidence

ORD record
ord-00a6f20449e9467787ccff744cdd5abc
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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