Acetone → HCID 67321086, compound

HRID 358311Notes

Reaction equation

HRID 358311 reaction equation
[CH3:1][C:2]([CH3:4])=[O:3].B(F)(F)F.[CH2:9]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]/[CH:22]=[CH:23]\[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH:10]1[O:12][CH2:11]1.C(OCC1OC1)C1OC1.C(=O)(O)[O-].[Na+]>CCOCC>[CH3:1][C:2]1([CH3:4])[O:12][CH:10]([CH2:9][O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]/[CH:22]=[CH:23]\[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:11][O:3]1

Participants

7

Reactant 5

HCID 180AcetoneHCID 6356Boron trifluorideHCID 16704Diglycidyl ether3×HCID 516892Sodium BicarbonateHCID 6435878Oxirane, 2-[[(9Z)-9-octadecen-1-yloxy]methyl]-

Product 1

HCID 67321086HCID 67321086, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Into a round bottom flask having a capacity of 500 ml and equipped with a reflux condenser, a thermometer, a dropping funnel, a nitrogen gas supply tube, and a stirring means, 81.2 g (1.4 moles) of acetone, and 2.0 g (0.014 mole) of boron trifluoride etharate were charged and stirred while supplying a nitrogen gas. Then, 64.9 g (0.2 mole) of oleyl glycidyl ether was gradually added dropwise while supplying a nitrogen gas. The reaction mixture generates heat as the glycidyl ether is added. Therefore, the reaction mixture was cooled to maintain a temperature of from 20° to 30° C., and it took about one hour for the addition of the glycidyl ether. The stirring was continued for further one hour. After confirming by the gas chromatograph of the reaction mixture that the glycidyl ether completely disappeared, the reaction mixture was poured into a dilute aqueous solution of sodium bicarbonate whereby the acid was neutralized. Ether was added thereto and the mixture was stirred, and thereafter the ether layer was collected by separation. Anhydrous sodium sulfate was added for dehydration, and the solvent was removed by distillation under a reduced pressure thereby to obtain 68.8 g (yield: 90%) of colourless, transparent 2,2-dimethyl-4-oleyloxymethyl- 1,3-dioxolan.

Workup

  1. customInto a round bottom flask having
  2. customa capacity of 500 ml and equipped with a reflux condenser
  3. additionis added
  4. temperatureTherefore, the reaction mixture was cooled
  5. temperatureto maintain a temperature of from 20° to 30° C., and it
  6. stirringthe mixture was stirred
  7. customthe ether layer was collected by separation
  8. additionAnhydrous sodium sulfate was added for dehydration
  9. customthe solvent was removed by distillation under a reduced pressure

Sources & evidence

ORD record
ord-70008f4373ea41da99ddb88554680db1
Source dataset
uspto-grants-1984_08
Patent number
US04465869

Reaction notes

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