Propylene Glycol → HCID 54117512, compound

HRID 1464415Notes

Reaction equation

HRID 1464415 reaction equation
N1C=CC=CC=1.[CH2:7]([OH:11])[CH:8]([OH:10])[CH3:9].[C:12]([O:16][O:17][C:18]([CH2:20][CH2:21][C:22](Cl)=[O:23])=[O:19])([CH3:15])([CH3:14])[CH3:13]>C(Cl)Cl>[C:18]([O:17][O:16][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:19])[CH2:20][CH2:21][C:22]([O:11][CH2:7][CH:8]([OH:10])[CH3:9])=[O:23]

Participants

5

Reactant 3

HCID 1030Propylene GlycolHCID 1049PyridineHCID 12329418tert-Butyl 4-chloro-4-oxobutaneperoxoate

Product 1

HCID 54117512HCID 54117512, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
10 °C

Procedure

A 250 mL 3-neck round-bottom flask, equipped with a magnetic stirrer, a thermometer, a cold water condenser and an addition funnel, was charged with 50 mL of methylene chloride, 4.2 g (0.052 mole) of pyridine and 19.0 g (0.25 mole) of 1,2-propanediol. The resulting vigorously stirred solution was cooled to 10° C. and to it was slowly added a solution of 11.5 g (0.050 mole) of 94% 3-(t-butylperoxycarbonyl)propionyl chloride in 10 mL of methylene chloride over a period of 20 minutes. The reaction mass was warmed to 20° C. and stirred at 20° C. for 210 minutes. The reaction mixture was washed at 10°-15° C. with 50 mL of aqueous 5% HCl solution and then twice with 100 mL portions of 5% aqueous NaHCO3 solution. The methylene chloride 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 12.4 g (100% of theory, uncorrected) of a straw-color liquid. An infrared spectrum of the product showed a strong OH band, a strong and broad carbonyl band at ca. 1720-1780 cm-1 and a strong --OO-- band at ca. 850 cm-1. The product has a peroxyester Act[O] content of 6.29%. Based on a theoretical Act[O] of 6.45% for the desired title product, the assay was 97.5% and the corrected yield was 97.5%.

Workup

  1. customA 250 mL 3-neck round-bottom flask, equipped with a magnetic stirrer
  2. customThe reaction
  3. temperaturemass was warmed to 20° C.
  4. washThe reaction mixture was washed at 10°-15° C. with 50 mL of aqueous 5% HCl solution
  5. dry with materialThe methylene chloride solution was then dried over 10% by weight of anhydrous MgSO4
  6. customafter separation of the spent desiccant
  7. filtrationby filtration
  8. customthe solvent was removed in vacuo
  9. customleaving 12.4 g (100% of theory, uncorrected) of a straw-color liquid

Sources & evidence

ORD record
ord-832ff03c45444177bb605196cceae8b6
Source dataset
uspto-grants-1994_04
Patent number
US05304649

Reaction notes

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