4-Toluenesulfonyl chloride → 3-(4-Methylphenyl)sulfonyloxypropyl 4-methylbenzenesulfonate

HRID 1913850Notes

Reaction equation

HRID 1913850 reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[CH2:12]([OH:16])[CH2:13][CH2:14][OH:15]>N1C=CC=CC=1>[CH3:8][C:7]1[CH:9]=[CH:10][C:4]([S:1]([O:15][CH2:14][CH2:13][CH2:12][O:16][S:1]([C:4]2[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=2)(=[O:3])=[O:2])(=[O:3])=[O:2])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 104421,3-Propanediol

Product 1

HCID 2303703-(4-Methylphenyl)sulfonyloxypropyl 4-methylbenzenesulfonateYield 83%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a solution of 116.36 g (610.37 mmol) of tosyl chloride in 200 mL of anhydrous pyridine add 19.26 g (253.09 mmol) of 1,3-propanediol in 50 mL of anhydrous pyridine dropwise over the period of two hours at 0-10° C. Stir the reaction mixture for an additional four hours, then pour it into 500 mL of ice cold water. Collect the white precipitate that forms by filtration, wash filter cake with water, dilute aqueous sulfuric acid (10 wt. %), dilute aqueous sodium carbonate (1M), and again with water. Crystallize the wet product from acetone to afford 80.68 g (83%) of 1,3-propanediol bis(4-methylbenzenesulfonate) as off white powder. 1H NMR (400 MHz, CDCl3) δ 7.77-7.69 (m, 4H), 7.37-7.30 (m, 4H), 4.05 (t, J=6.0 Hz, 4H), 2.44 (s, 6H), 1.99 (p, J=6.0 Hz, 2H). 13C{1H} NMR (101 MHz, CDCl3) δ 145.01, 132.65, 129.92, 127.84, 65.83, 28.67, 21.61. MS (m/e): 408 (M+Na).

Workup

  1. customCollect the white precipitate that forms
  2. filtrationby filtration
  3. washwash
  4. filtrationfilter cake with water, dilute aqueous sulfuric acid (10 wt. %), dilute aqueous sodium carbonate (1M)
  5. customCrystallize the wet product from acetone

Sources & evidence

ORD record
ord-a540d2e8b6a04a86a9e58ac30c6a5fff
Source dataset
uspto-grants-2013_12
Patent number
US08609794B2

Reaction notes

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