Acetone → HCID 12892725, compound

HRID 1879094Notes

Reaction equation

HRID 1879094 reaction equation
C[C:2]1(C)[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][CH2:4][C:3]1=[O:10].Cl.[CH3:13]C(C)=O>[Cl-].[Na+].O>[CH3:9][C:6]1([CH:8]=[CH2:13])[CH2:7][CH2:2][C:3](=[O:10])[CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 583881972,2,4,4-Tetramethylcyclohexan-1-one

Product 1

HCID 12892725HCID 12892725, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred solution of 2 (1.98 mmol, 360 mg) in acetone (7.76 mL) was added 10% aqueous hydrochloric acid solution (3.02 mL), and the resulting mixture was stirred at room temperature for 2.5 hours. The reaction mixture was then diluted with brine (40 mL) and extracted with methylene chloride/ethyl ether (1:2, 3×30 mL). The organic layers were combined and washed with saturated aqueous sodium bicarbonate solution (2×30 mL) and brine (1×30 mL), then dried over magnesium sulfate, filtered, and concentrated in vacuo to give 19 (251.6 mg, 1.92 mmol, 94%) as a yellow oil that was used in the next reaction without further purification: 1H NMR (CDCl3) δ 5.89 (1H, dd, J=0.5, 17.3 Hz), 5.15 (1H, dd, J=1, 3.5 Hz), 5.12 (1H, dd, J=0.5, 10 Hz), 2.42-2.28 (4H, m), 1.97-1.91 (2H, m), 1.74-1.68 (2H, m), 1.12 (3H, s); 13C NMR (CDCl3) δ 212.4, 145.5, 112.9, 38.2, 37.1, 27.4; MS (EI) m/z 138.1 [M+], 123.1, 110.1, 105.1, 97.1, 86.0 (100%), 68.1, 63.0, 54.9; HRMS (EI) calcd for C9H14O 138.1045 found 138.1048.

Workup

  1. extractionextracted with methylene chloride/ethyl ether (1:2, 3×30 mL)
  2. washwashed with saturated aqueous sodium bicarbonate solution (2×30 mL) and brine (1×30 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4235b2156f0b480e8d76e36af82c290d
Source dataset
uspto-grants-2012_11
Patent number
US08314137B2

Reaction notes

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