Water → 2-(Prop-2-en-1-yl)cyclododecan-1-one

HRID 2413359Notes

Reaction equation

HRID 2413359 reaction equation
[OH-].[Na+].[C:3]1(=[O:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH2:16](Cl)[CH:17]=[CH2:18].O>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:18]([CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:3]1=[O:15])[CH:17]=[CH2:16]

Participants

7

Reactant 4

HCID 962WaterHCID 7850Allyl chlorideHCID 13246CyclododecanoneHCID 14798Sodium Hydroxide

Product 1

HCID 124038542-(Prop-2-en-1-yl)cyclododecan-1-one

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

40 g (1 mole) of sodium hydroxide platelets, 182 g (1 mole) of cyclododecanone dissolved in 200 ml of toluene, and 10 g of tetrabutylammonium bromide are placed in a 500 ml three-necked flask provided with a stirrer, reflux cooler and dropping funnel. Over a period of one hour, 1 mole of allyl chloride is added dropwise, with stirring, at a reaction-mixture temperature of from 70° to 80° C. The reaction mixture is subsequently stirred for a further 5 hours at 80° C. and finally 200 ml of water are added and the phases are separated. The organic phase is then washed until neutral with a further 100 ml of water and subsequently distilled. After the low-boiling components have been drawn off, unreacted cyclododecanone is first distilled off. Finally, at 0.01 torr and from 82° to 84° C., the desired 2-(2-propenyl)-cyclododecanone is obtained as a colorless liquid in a yield of 149.8 g, corresponding to 67.5% of the theoretical yield.

Workup

  1. customprovided with a stirrer
  2. temperaturereflux cooler
  3. stirringThe reaction mixture is subsequently stirred for a further 5 hours at 80° C.
  4. customthe phases are separated
  5. washThe organic phase is then washed until neutral with a further 100 ml of water
  6. distillationsubsequently distilled
  7. distillationunreacted cyclododecanone is first distilled off

Sources & evidence

ORD record
ord-759b61fea8c142d5b58a9aef7d60b1ac
Source dataset
uspto-grants-1985_01
Patent number
US04496748

Reaction notes

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