Allyl Alcohol → HCID 54483562, compound

HRID 361955Notes

Reaction equation

HRID 361955 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[C:7]([O:11][O:12][C:13]([CH3:19])([CH3:18])[CH2:14][CH:15]([CH3:17])[OH:16])([CH3:10])([CH3:9])[CH3:8].[CH2:20]([OH:23])[CH:21]=[CH2:22]>C(OCC)(=O)C>[C:1]([O:23][CH2:20][CH:21]=[CH2:22])(=[O:5])[C:2]([O:16][CH:15]([CH3:17])[CH2:14][C:13]([O:12][O:11][C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:18])[CH3:19])=[O:3]

Participants

5

Reactant 3

HCID 7858Allyl Alcohol2×HCID 65578Oxalyl chlorideHCID 220654633-t-Butylperoxy-1,3-dimethylbutanol

Product 1

HCID 54483562HCID 54483562, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A second preparation of I-4 was carried out. A 100 mL 3-necked flask equipped with a magnetic stirring bar, a nitrogen inlet line, a thermometer and an addition funnel with a side arm was charged with 25.9 g(200 mmoles) of oxalyl chloride, dry nitrogen gas was bubbled through the oxalyl chloride and the flask contents were cooled to 0° C. Then 20.0 g (97.3 mmoles) of 92.6% 3-t-butylperoxy-1,3-dimethylbutanol was added dropwise at such a rate that the temperature remained below 15° C. The addition took 30 minutes to complete. The reaction mass was then stirred for 60 minutes at 15° C. after which 50 mL of dry ethyl acetate was added. The contents were then transferred to a one-necked flask and the solvent and excess oxalyl chloride were then removed using a rotary evaporator. Obtained was 29.3 g of a light yellow oil. The oil was cooled to 10° C. and to it was added 6.0 g (103.3 mmoles) of allyl alcohol over a period of 15 minutes while a vigorous stream of dry nitrogen was swept through the reaction mass. The temperature was held below 20° C. during the addition of allyl alcohol. The reaction mixture was then stirred for 60 minutes at 15°-20° C. after which it was stripped on a rotary evaporator. Obtained was 31.7 g (>100% of theory, uncorrected) of a light yellow liquid. GC showed a single large peak, 93% by area. An IR spectrum of the product showed carbonyl bands at 1770 cm-1 and 1750 cm-1 and a peroxide (--OO--) band at 875 cm-1.

Workup

  1. customA second preparation of I-4
  2. customA 100 mL 3-necked flask equipped with a magnetic stirring bar, a nitrogen inlet line
  3. customwas bubbled through the oxalyl chloride
  4. customremained below 15° C
  5. additionThe addition
  6. additionwas added
  7. customThe contents were then transferred to a one-necked flask
  8. customthe solvent and excess oxalyl chloride were then removed
  9. customa rotary evaporator
  10. customObtained
  11. temperatureThe oil was cooled to 10° C. and to it
  12. customwas stripped on a rotary evaporator
  13. customObtained

Sources & evidence

ORD record
ord-eb15086359484a1380dc6c740b10d0ac
Source dataset
uspto-grants-1999_02
Patent number
US05866712

Reaction notes

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