4-Toluenesulfonyl chloride → 1,1,1-Tris(tosylethoxymethyl)ethane

HRID 36829Notes

Reaction equation

HRID 36829 reaction equation
O[CH2:2][CH2:3][O:4][CH2:5][C:6]([CH2:13][O:14][CH2:15][CH2:16]O)([CH2:8][O:9][CH2:10][CH2:11]O)[CH3:7].[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>N1C=CC=CC=1>[S:24]([CH2:16][CH2:15][O:14][CH2:13][C:6]([CH2:5][O:4][CH2:3][CH2:2][S:24]([C:21]1[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=1)(=[O:26])=[O:25])([CH2:8][O:9][CH2:10][CH2:11][S:24]([C:21]1[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=1)(=[O:26])=[O:25])[CH3:7])([C:21]1[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=1)(=[O:26])=[O:25]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 22328182Poly(oxy-1,2-ethanediyl), α-hydro-ω-hydroxy-, ether with 2-(hydroxymethyl)-2-methyl-1,3-propanediol (3:1)

Product 1

HCID 545380091,1,1-Tris(tosylethoxymethyl)ethaneYield 50%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1,1,1-tris(hydroxyethoxymethyl)ethane (6.7 g, 0.026 mol) in 35 mL of anhydrous pyridine was cooled to -10° C. Then solid p-toluenesulfonyl chloride (16.6 g, 0.087 mol) was added in portions over 1.5 hrs. The mixture was kept at -10° C. for 15 hrs. The resulting slurry was partitioned between dichloromethane (100 mL) and water (50 mL) and the layers were separated. The organic layer was washed with water (50 mL), dried over anhydrous sodium sulfate and evaporated to give a crude gum. This material was purified over silica gel using 1% methanol/dichloromethane as eluant to give 1,1,1-tris(tosylethoxymethyl)ethane (8.9 g, 0.013 mol, 47%).

Workup

  1. customThe resulting slurry was partitioned between dichloromethane (100 mL) and water (50 mL)
  2. customthe layers were separated
  3. washThe organic layer was washed with water (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customto give a crude gum
  7. customThis material was purified over silica gel using 1% methanol/dichloromethane as eluant

Sources & evidence

ORD record
ord-c7b29fdc701a4a23a41d1576ba2c2b8d
Source dataset
uspto-grants-1995_05
Patent number
US05417959

Reaction notes

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