Acetone → 2,6,6-Trimethylfulvene

HRID 2216718Notes

Reaction equation

HRID 2216718 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][CH2:4][CH:3]=1.[CH3:7][C:8]([CH3:10])=O.N1CCCC1.OP(O)(O)=O>C(O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5](=[C:8]([CH3:10])[CH3:7])[CH:6]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 1004Phosphoric AcidHCID 31268PyrrolidineHCID 1380262-Methyl-1,3-cyclopentadiene

Product 1

HCID 143632822,6,6-Trimethylfulvene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-methyl-1,3-cyclopentadiene (125 g, 1.56 mol) in 1.2 L of ethanol was treated at low temperature with 126 mL (1.72 mol) of acetone and 142 mL (1.72 mol) of pyrrolidine. The resulting solution was kept below room temperature overnight. Then the reaction mixture was neutralized with a 10% aq. solution of H3PO4, extracted with hexane (3×150 mL) and washed with water until neutral pH. The organic phase was separated, dried with MgSO4 and concentrated. The residue was distilled at 70° C./60 mmHg. Yield 112.6 g (60%).

Workup

  1. extractionextracted with hexane (3×150 mL)
  2. washwashed with water until neutral pH
  3. customThe organic phase was separated
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated
  6. distillationThe residue was distilled at 70° C./60 mmHg

Sources & evidence

ORD record
ord-0ea6ee23bbb54644b791afdbeddc273d
Source dataset
uspto-grants-2006_09
Patent number
US07112638B2

Reaction notes

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