2,2-Dimethoxypropane → NSC650609

HRID 380061Notes

Reaction equation

HRID 380061 reaction equation
[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][OH:5].O.[C:11]1(C)[CH:16]=CC(S(O)(=O)=O)=C[CH:12]=1.COC(OC)(C)C>CN(C)C=O>[CH3:12][C:11]1([CH3:16])[O:5][CH2:4][C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:2][O:1]1

Participants

5

Reactant 3

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

Product 1

HCID 373708NSC650609

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

Pentaerythritol (50 g, 0.36 mol) and p-toluenesulfonic acid monohydrate (0.61 g) were dissolved in 500 ml N,N-dimethylformamide (DMF, dried by molecular sieve at room temperature) at about 80° C., and then the mixture was allowed to cool undisturbed. When the solution cooled to about 40° C., stirring was started and 55.4 ml 2,2-dimethoxypropane (0.36 mol) was added. After 24 hours of stirring at room temperature, the solution was stirred at room temperature with 9.0 g of base treated DOWEX 1XZ-100 ion-exchange resin for 1 hour, filtered and then the solvent was evaporated under reduced pressure at 85° C. The base treated DOWEX 1XZ-100 ion exchange was prepared by washing 30 g. twice with 200 ml of deionized water, then washed with 300 ml of 4% aq. NaOH and then washed three times with 200 ml of water, filtered and then air-dried in a hood. After the treatment with this resin as noted above, the dry product was ground and extracted (Soxhlet), first with light petroleum ether (b.p. 40-60° C.) for 6 hours, then with diethyl ether for 12 hours, collected and dried. Yield: White crystals (40.0 g, 61.9%). M.P. 124.5°-125.5° C.; 11H-NMR (300 MHz, DMSO-d6) 1.28 ppm (s, 6H), 3.34 ppm (d, J=5.7 Hz, 4H), 3.58 ppm (s, 4H), 4.47 ppm (t, J=5.4 Hz, 2H);

Workup

  1. temperatureto cool undisturbed
  2. stirringAfter 24 hours of stirring at room temperature
  3. additiontreated DOWEX 1XZ-100 ion-exchange resin for 1 hour
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure at 85° C
  6. additionThe base treated DOWEX 1XZ-100 ion exchange
  7. customwas prepared
  8. washby washing 30 g
  9. washtwice with 200 ml of deionized water, then washed with 300 ml of 4% aq. NaOH
  10. washwashed three times with 200 ml of water
  11. filtrationfiltered
  12. customair-dried in a hood
  13. extractionextracted (Soxhlet)
  14. waitwith diethyl ether for 12 hours
  15. customcollected
  16. customdried

Sources & evidence

ORD record
ord-2481fc35e210474ba1d163d04b0a170e
Source dataset
uspto-grants-2001_10
Patent number
US06300458B1

Reaction notes

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