Acetone → HCID 20430924, compound

HRID 2413360Notes

Reaction equation

HRID 2413360 reaction equation
CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-].[CH2:14]([CH:17]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][C:18]1=[O:29])[CH:15]=[CH2:16].CC(C)=O>C(O)(C)C>[CH2:14]([CH:17]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1[OH:29])[CH:15]=[CH2:16]

Participants

5

Reactant 3

HCID 180AcetoneHCID 11143Aluminum isopropoxideHCID 124038542-(Prop-2-en-1-yl)cyclododecan-1-one

Product 1

HCID 20430924HCID 20430924, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

0.1 mole of aluminum isopropoxide in 500 ml of isopropanol is placed in a three-necked flask provided with a stirrer and a Vigreux column. The mixture is refluxed. A 25% by weight solution of 2-(2-propenyl)-cyclododecanone in isopropanol is added dropwise to the boiling reaction mixture, over a period of 12 hours. The acetone produced, which serves at the same time as indicator for the progress of the reaction, is collected at the top of the column. After approximately a further hour of refluxing, the reaction is complete. After the isopropanol has been drawn off, the reaction mixture is hydrolyzed with 6N hydrochloric acid. Extraction is then carried out with 200 ml of toluene and the organic phase is worked up by distillation. Finally, 2-(2-propenyl)-cyclododecanol is obtained as a colorless liquid in a yield of 95% of the theoretical yield at a boiling range of from 172° to 175° C. at 12 torr.

Workup

  1. customprovided with a stirrer
  2. temperatureThe mixture is refluxed
  3. customwhich serves at the same time as indicator for the progress of the reaction
  4. customis collected at the top of the column
  5. temperatureAfter approximately a further hour of refluxing
  6. extractionExtraction
  7. distillationthe organic phase is worked up by distillation

Sources & evidence

ORD record
ord-4bc30aa1957644d299dcf496eefaf75f
Source dataset
uspto-grants-1985_01
Patent number
US04496748

Reaction notes

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