Dimethylformamide → NSC650609

HRID 2410467Notes

Reaction equation

HRID 2410467 reaction equation
[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][OH:5].CN(C)C=O.CO[C:17](OC)([CH3:19])[CH3:18].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(N(CC)CC)C>[CH3:18][C:17]1([CH3:19])[O:5][CH2:4][C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:2][O:1]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 64952,2-DimethoxypropaneHCID 8285PentaerythritolHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 373708NSC650609

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
25 °C

Procedure

Into a 5 L round-bottom flask fitted with a thermometer, a nitrogen-introducing tube, and a stirrer were charged 254 g of pentaerythritol and 2,500 g of N,N-dimethylformamide, and they were heated and dissolved at 80° C. After cooling to 25° C., 195 g of 2,2-dimethoxypropane and 3.6 g of p-toluenesulfonic acid monohydrate were placed therein and, with introduction of nitrogen thereinto, a reaction was carried out at 25° C. without further treatment. Neutralization was performed by adding 9.5 g of triethylamine and the reaction solution was concentrated. After concentration, the resulting powder was dispersed in 1 kg of hexane, followed by stirring and filtration. The hexane-washing step was repeated four times. The resulting cake was dissolved in 1 kg of ethyl acetate at 50° C. and, after insoluble matter was filtrated, 250 g of Kyoward 2003 was added to the filtrate and adsorption treatment was performed at 50° C. for 1 hour. The filtrate was concentrated to obtain 2,2-dimethyl-5,5-bis(hydroxymethyl)-1,3-dioxane. 1H-NMR (D2O, internal standard H2O=4.65 ppm) δ (ppm): 1.40 (6H, s, —CH3), 2.69, 3.64 (4H, 4H, s, s, —O—CH2—C—, —CH2OH)

Workup

  1. customInto a 5 L round-bottom flask fitted with a thermometer
  2. additiona nitrogen-introducing tube, and a stirrer
  3. temperaturewere heated
  4. dissolutiondissolved at 80° C
  5. customwas carried out at 25° C. without further treatment
  6. concentrationthe reaction solution was concentrated
  7. concentrationAfter concentration
  8. additionthe resulting powder was dispersed in 1 kg of hexane
  9. filtrationfiltration
  10. washThe hexane-washing step
  11. dissolutionThe resulting cake was dissolved in 1 kg of ethyl acetate at 50° C.
  12. filtrationafter insoluble matter was filtrated
  13. addition250 g of Kyoward 2003 was added to the filtrate and adsorption treatment
  14. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-28ada08f750949c6916ba6fa894fdabb
Source dataset
uspto-grants-2014_08
Patent number
US08816099B2

Reaction notes

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