Acetic Acid → HCID 54067917, compound

HRID 1978261Notes

Reaction equation

HRID 1978261 reaction equation
[CH3:1][C:2]12[CH2:7][CH:6]1[CH2:5][CH:4]([CH2:8][CH:9]=O)[C:3]2([CH3:12])[CH3:11].C[O-].[Na+].[CH:16](=[O:19])[CH2:17][CH3:18].C(O)(=O)C>CO>[CH3:18][C:17](=[CH:9][CH2:8][CH:4]1[CH2:5][CH:6]2[C:2]([CH3:1])([CH2:7]2)[C:3]1([CH3:12])[CH3:11])[CH:16]=[O:19]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 527PropanalHCID 10942334Sodium MethoxideHCID 21707621HCID 21707621, compound

Product 1

HCID 54067917HCID 54067917, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

30 g (0.18 mol) of (1,2,2-trimethylbicyclo[3.1.0]hex-3-yl)ethanal was added to 5.0 ml (24 mmol) of stirred 5.4 M methanolic solution of sodium methylate diluted with 40 ml of methanol. 35 g (0.61 mol) of propionaldehyde was added at 25° C. with cooling during 10 minutes, the reaction mixture stirred at room temperature for 1.5 hours, neutralized with acetic acid and the solvent removed in vacuo. The residue was dissolved in 100 ml of ether, washed with 3×80 ml of water, dried (MgSO4) and evaporated in vacuo. Purification by Kugelrohr distillation at 94° C./0.1 Torr followed by flash chromatography on silica gel (eluent: hexane/MTBE 4:1) gave 16.0 g (43% yield) of 2-methyl-4-(1,2,2-trimethylbicyclo[3.1.0]hex-3-yl)but-2-enal.

Workup

  1. temperaturewith cooling during 10 minutes
  2. customthe solvent removed in vacuo
  3. dissolutionThe residue was dissolved in 100 ml of ether
  4. washwashed with 3×80 ml of water
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. customPurification
  8. distillationby Kugelrohr distillation at 94° C./0.1 Torr

Sources & evidence

ORD record
ord-456bb3546db2489ea319fbcecc46c131
Source dataset
uspto-grants-2001_05
Patent number
US06235943B1

Reaction notes

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