2-Methyl-2-nitro-1,3-propanediol → 2-Methyl-2-nitro-1,3-propanediol-di-p-toluenesulfonate

HRID 2060936

Reaction equation

HRID 2060936 reaction equation
[CH3:1][C:2]([N+:7]([O-:9])=[O:8])([CH2:5][OH:6])[CH2:3][OH:4].C(N([CH2:15][CH3:16])CC)C.[S:17](Cl)([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18]>C(OCC)C>[S:17]([O:4][CH2:3][C:2]([CH3:1])([N+:7]([O-:9])=[O:8])[CH2:5][O:6][S:17]([C:16]1[CH:15]=[CH:24][C:23]([CH3:25])=[CH:22][CH:21]=1)(=[O:19])=[O:18])([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 64802-Methyl-2-nitro-1,3-propanediolHCID 73974-Toluenesulfonyl chlorideHCID 8471Triethylamine

Product 1

HCID 5195532-Methyl-2-nitro-1,3-propanediol-di-p-toluenesulfonateYield 5.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-methyl-2-nitro-1,3-propanediol (80 g, 0.592 mol) and triethylamine (131.8 g, 1.303 mol) in diethyl ether (250 ml) is added a solution of tosyl chloride (225.7 g, 1.184 mol) in diethyl ether (800 ml) between −15° and −20° C. The resulting suspension is stirred at 0° C. for 1 hour, then 18 hours at ambient temperature. The reaction mixture is filtered, the solid residue is taken up twice in ethyl acetate and stirred, the suspension being filtered again. The combined ethyl acetate layers are evaporated to dryness giving a first crop of crude product (175.8 g). The ether filtrate is washed with water (2×) and brine, dried (Na2SO4), filtered, and partly concentrated. The suspension is filtered giving another 15.0 g of product. The crude solid product (190.8 g, 73%) is used in the next step without further purification.

Workup

  1. custom18 hours
  2. customat ambient temperature
  3. filtrationThe reaction mixture is filtered
  4. stirringstirred
  5. filtrationthe suspension being filtered again
  6. customThe combined ethyl acetate layers are evaporated to dryness
  7. customgiving a first crop of crude product (175.8 g)
  8. washThe ether filtrate is washed with water (2×) and brine
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationpartly concentrated
  12. filtrationThe suspension is filtered

Sources & evidence

ORD record
ord-32974668cc244d5bbec78c16528d8615
Source dataset
uspto-grants-2012_10
Patent number
US08278464B2

Linked notes

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