Methyl Ethyl Ketone → HCID 53673391, compound

HRID 1978264Notes

Reaction equation

HRID 1978264 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+]>O.CO>[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 3

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

Product 1

HCID 53673391HCID 53673391, compoundYield 45.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 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 1.4 l of methanol. The reaction mixture was stirred overnight with ice-bath cooling, poured into 3 l 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-0b8641a73a2b440f9ab1c259ece31a0f
Source dataset
uspto-grants-2001_05
Patent number
US06235943B1

Reaction notes

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