Acetone → 3-(1,1,3-Trimethylbutyl)-6,6-dimethylfulvene

HRID 495745Notes

Reaction equation

HRID 495745 reaction equation
[CH3:1][C:2]([C:8]1[CH2:12][CH:11]=[CH:10][CH:9]=1)([CH3:7])[CH2:3][CH:4]([CH3:6])[CH3:5].[CH3:13][C:14]([CH3:16])=O.N1CCCC1.CCOCC>CO.O>[CH3:7][C:2]([C:8]1[CH:12]=[CH:11][C:10](=[C:14]([CH3:16])[CH3:13])[CH:9]=1)([CH3:1])[CH2:3][CH:4]([CH3:6])[CH3:5]

Participants

7

Reactant 4

HCID 180AcetoneHCID 3283Diethyl EtherHCID 31268PyrrolidineHCID 22327806HCID 22327806, compound

Product 1

HCID 223277773-(1,1,3-Trimethylbutyl)-6,6-dimethylfulveneYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3.00 g (18.3 mmol) of (1,1,3-trimethylbutyl)cyclopentadiene in 30 ml of methanol, 13.4 ml (182.5 mmol) of acetone and 3.1 ml (36.6 mmol) of pyrrolidine were added with ice cooling, followed by stirring at room temperature for one night. After the reaction solution was diluted with % 100 ml of ether, 50 ml of water was added. The organic phase was separated, washed with water and a saturated saline solution, then dried over anhydrous magnesium sulfate and filtered. From the filtrate, the solvent was removed under reduced pressure to obtain a liquid. The liquid was subjected to vacuum distillation (130° C./1 mmHg) to obtain 3.50 g (17.1 mmol) of a yellow liquid (yield: 94%). The analyzed values are given below.

Workup

  1. additionwas added
  2. customThe organic phase was separated
  3. washwashed with water
  4. dry with materiala saturated saline solution, then dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customFrom the filtrate, the solvent was removed under reduced pressure
  7. customto obtain a liquid
  8. distillationThe liquid was subjected to vacuum distillation (130° C./1 mmHg)

Sources & evidence

ORD record
ord-71697aff8bd043429b19e750e4aed7fa
Source dataset
uspto-grants-2005_09
Patent number
US06939928B1

Reaction notes

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