Acetone → HCID 21943910, compound

HRID 2216720Notes

Reaction equation

HRID 2216720 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH3:9])[CH2:7][CH:8]=1)([CH3:3])[CH3:2].[OH-].[Na+].[CH3:12][C:13]([CH3:15])=O.OP(O)(O)=O>C1COCC1>[CH3:9][C:6]1[C:7](=[C:13]([CH3:15])[CH3:12])[CH:8]=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 1004Phosphoric AcidHCID 14798Sodium HydroxideHCID 15865176HCID 15865176, compound

Product 1

HCID 21943910HCID 21943910, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-isopropyl-1methyl-1,3-cyclopentadiene (39 g, 0.32 mol) was added at low temperature to a suspension of 12.8 g (0.32 mol) of sodium hydroxide in 200 mL of dry THF. After 30 min stirring, the reaction mixture was treated with 23.8 mL (0.32 mol) of acetone. The resulting solution was kept below room temperature overnight. Then the resulting mixture was neutralized with a 10% aq. solution of H3PO4, extracted with hexane (3×100 mL) and washed with water until neutral pH. The organic phase was separated, dried with MgSO4 and concentrated. The residue was distilled at 80° C./10 mmHg. Yield 25.96 g (50%).

Workup

  1. waitThe resulting solution was kept below room temperature overnight
  2. extractionextracted with hexane (3×100 mL)
  3. washwashed with water until neutral pH
  4. customThe organic phase was separated
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated
  7. distillationThe residue was distilled at 80° C./10 mmHg

Sources & evidence

ORD record
ord-79ddd5da66594d9ca627e24c43249a8b
Source dataset
uspto-grants-2006_09
Patent number
US07112638B2

Reaction notes

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