Propylene Glycol → HCID 54421203, compound

HRID 2399830Notes

Reaction equation

HRID 2399830 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. customat 20° C.
  3. additionDuring the addition there
  4. customa white precipitate formed
  5. customThe reaction
  6. customThe precipitate was separated by filtration
  7. washthe white solid was-washed with about 25 mL of methyl t-butyl ether
  8. washthe filtrate was washed twice with 50 mL portions of 5% aqueous HCl solution
  9. dry with materialThe methyl t-butyl ether solution was then dried over 10% by weight of anhydrous MgSO4
  10. customafter separation of the spent desiccant
  11. filtrationby filtration
  12. customthe solvent was removed in vacuo
  13. customleaving 17.4 g (98.3% of theory, uncorrected) of a straw-color liquid

Sources & evidence

ORD record
ord-a07c8344a6cf4e9c923e38c4785c13f3
Source dataset
uspto-grants-1995_09
Patent number
US05451654

Reaction notes

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