Acetone → 1,6,6-Trimethyl-3-tert-butyl-fulvene

HRID 495724

Reaction equation

HRID 495724 reaction equation
[C:1]([C:5]1[CH2:9][CH:8]=[C:7]([CH3:10])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:11]C(C)=O.N1CCCC1.C(O[CH2:23][CH3:24])C>CO.O>[C:1]([C:5]1[CH:11]=[C:23]([CH3:24])[C:8](=[C:7]([CH3:6])[CH3:10])[CH:9]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 180AcetoneHCID 3283Diethyl EtherHCID 31268PyrrolidineHCID 153198441-Tert-butyl-3-methylcyclopenta-1,3-diene

Product 1

HCID 27627611,6,6-Trimethyl-3-tert-butyl-fulvene

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 13.0 g (95.6 mmol) of 1-tert-butyl-3-methylcyclopentadiene in 130 ml of dehydrated methanol, 55.2 g (950.4 mmol) of dehydrated acetone was dropwise added in a nitrogen atmosphere at 0° C. with ice cooling, and 68.0 g (956.1 mmol) of pyrrolidine was further dropwise added, followed by stirring at room temperature for 4 days. After the reaction solution was diluted with 400 ml of diethyl ether, 400 ml of water was added. The organic phase was separated, washed with a 0.5N hydrochloric acid aqueous solution (150 ml×4), water (200 ml×3) and a saturated saline solution (150 ml), and then dried over anhydrous magnesium sulfate. The drying agent was filtered, and from the filtrate the solvent was distilled off to obtain a liquid. The liquid was subjected to vacuum distillation (70-80° C./0.1 mmHg) to obtain 10.5 g of a yellow liquid. The analyzed values are given below.

Workup

  1. additionwas further dropwise added
  2. additionwas added
  3. customThe organic phase was separated
  4. washwashed with a 0.5N hydrochloric acid aqueous solution (150 ml×4), water (200 ml×3)
  5. dry with materiala saturated saline solution (150 ml), and then dried over anhydrous magnesium sulfate
  6. filtrationThe drying agent was filtered
  7. distillationfrom the filtrate the solvent was distilled off
  8. customto obtain a liquid
  9. distillationThe liquid was subjected to vacuum distillation (70-80° C./0.1 mmHg)

Sources & evidence

ORD record
ord-0655bafe545c4163b57a20b2aaefd619
Source dataset
uspto-grants-2005_09
Patent number
US06939928B1

Linked notes

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