Propylene Glycol → HCID 54421203, compound

HRID 273871Notes

Reaction equation

HRID 273871 reaction equation
[C:1]([O:5][O:6][C:7]([C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11](Cl)=[O:12])=[O:8])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[CH2:24]([OH:28])[CH:25]([OH:27])[CH3:26]>C(OC)(C)(C)C>[C:7]([O:6][O:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:8])[C:9]1[C:10](=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:11]([O:28][CH2:24][CH:25]([OH:27])[CH3:26])=[O:12]

Participants

5

Reactant 3

HCID 1030Propylene GlycolHCID 1049PyridineHCID 12329419HCID 12329419, compound

Product 1

HCID 54421203HCID 54421203, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
25 °C

Procedure

A 300 mL 3-neck round-bottom flask, equipped with a magnetic stirrer, a thermometer, a cold water condenser and an addition funnel, was charged with 100 mL of methyl t-butyl ether, 16.7 g (0.06 mole) of 91.3% of 2-(t-butylperoxycarbonyl)benzoyl chloride and 5.5 g (0.07 mole) of pyridine. To this vigorously stirred solution at 20° C. was added 22.8 g (0.30 mole) of 1,2-propanediol over a period of 20 minutes. During the addition there was a slight exotherm and a white precipitate formed. The reaction mass was warmed to 25° C. and stirred at 25° C. for 240 minutes. The precipitate was separated by filtration and the white solid was washed with about 25 mL of methyl t-butyl ether. The methyl t-butyl ether washings were combined with the filtrate and the filtrate was washed twice with 50 mL portions of 5% aqueous HCl solution, then twice with 50 mL portions of 3% aqueous NaHCO3 solution. The methyl t-butyl ether solution was then dried over 10% by weight of anhydrous MgSO4 and, after separation of the spent desiccant by filtration, the solvent was removed in vacuo leaving 17.4 g (98.3% of theory, uncorrected) of a straw-color liquid. An infrared spectrum of the product showed a strong OH band at ca. 3500 cm-1 and two carbonyl bands at ca. 1720 cm-1 and 1770 cm-1. The product had a peroxyester Act[O] content of 5.02%. Based on a theoretical Act[O] of 5.40% for the desired title product, the assay was 93.0% and the corrected yield was 91.4%.

Workup

  1. customA 300 mL 3-neck round-bottom flask, equipped with a magnetic stirrer
  2. additionDuring the addition there
  3. customa white precipitate formed
  4. customThe reaction
  5. customThe precipitate was separated by filtration
  6. washthe white solid was washed with about 25 mL of methyl t-butyl ether
  7. washthe filtrate was washed twice with 50 mL portions of 5% aqueous HCl solution
  8. dry with materialThe methyl t-butyl ether solution was then dried over 10% by weight of anhydrous MgSO4
  9. customafter separation of the spent desiccant
  10. filtrationby filtration
  11. customthe solvent was removed in vacuo
  12. customleaving 17.4 g (98.3% of theory, uncorrected) of a straw-color liquid

Sources & evidence

ORD record
ord-dfaade5398344549a1c8d8f64af47f52
Source dataset
uspto-grants-1995_02
Patent number
US05387654

Reaction notes

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