Methanol → HCID 53673391, compound

HRID 1979121Notes

Reaction equation

HRID 1979121 reaction equation
[CH3:1][C:2](=[O:5])[CH2:3][CH3:4].[CH3:6][C:7]12[CH2:12][CH:11]1[CH2:10][CH:9]([CH2:13][CH:14]=O)[C:8]2([CH3:17])[CH3:16].[OH-].[K+].CO>O>[CH3:4][C:3](=[CH:14][CH2:13][CH:9]1[CH2:10][CH:11]2[C:7]([CH3:6])([CH2:12]2)[C:8]1([CH3:16])[CH3:17])[C:2](=[O:5])[CH3:1]

Participants

6

Reactant 4

HCID 887MethanolHCID 6569Methyl Ethyl KetoneHCID 14797Potassium HydroxideHCID 21707621HCID 21707621, compound

Product 1

HCID 53673391HCID 53673391, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

560 g (8.5 mol) of butan-2-one and 234 g (1.4 mol) of (1,2,2-trimethylbicyclo[3.1.0]hex-3-yl)ethanal were added to 48 g (0.75 mol) of potassium hydroxide dissolved in 500 ml of water and 1.41 of methanol. The reaction mixture was stirred overnight with ice-bath cooling, poured into 3 1, of water and extracted with diethyl ether. The extract was washed with water, dried (MgSO4) and evaporated in vacuo. The residue was distilled at 108° C./0.1 Torr to give 140 g (45% yield) of 3-methyl-5-(1,2,2-trimethylbicyclo[3.1.0]hex-3-yl)pent-3-en-2-one.

Workup

  1. temperaturecooling
  2. extractionextracted with diethyl ether
  3. washThe extract was washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. distillationThe residue was distilled at 108° C./0.1 Torr

Sources & evidence

ORD record
ord-b605bebd4e80428098160282426faaa7
Source dataset
uspto-grants-2001_05
Patent number
US06239314B1

Reaction notes

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