Ethyl Acetate → HCID 11389626, compound

HRID 1665927Notes

Reaction equation

HRID 1665927 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:11])[CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]1.[CH3:12][C:13](=O)[O:14]CC>C1(C)C=CC=CC=1>[C:13]([CH:6]1[CH2:5][C:4]([CH3:11])([CH3:3])[CH2:9][CH2:8][C:7]1=[O:10])(=[O:14])[CH3:12]

Participants

5

Reactant 3

HCID 8857Ethyl Acetate2×HCID 24758Sodium hydrideHCID 138166Cyclohexanone, 4,4-dimethyl-

Product 1

HCID 11389626HCID 11389626, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
55 °C

Procedure

To a suspension of NaH (2.88 g, 60% dispersion in mineral oil, 60 mmol) in toluene (25 mL), EA (6.5 mL, 66 mmol) is added. The mixture is stirred at rt for 5 min before a solution of 4,4-dimethyl-cyclohexanone (2.52 g, 20 mmol) in EA (6 mL) is added. The mixture is heated to 55° C. where a vigorous reaction starts. The white to grey suspension turns orange and becomes clear. The clear solution is poured onto ice/water and is extracted with EA. The aq. phase is acidified to pH 4-5 and extracted once more with EA. The combined organic extracts are dried over Na2SO4 and the solvent is removed in vacuo to give 2-acetyl-4,4-dimethyl-cyclohexanone (2.00 g) as a yellow oil; 1H NMR (CDCl3): δ 2.35 (t, J=7.0 Hz, 2H), 2.12 (s, 2H), 2.10 (s, 1H), 1.48 (t, J=7.0 Hz, 2H), 0.98 (s, 6H).

Workup

  1. additionis added
  2. additionis added
  3. customa vigorous reaction
  4. additionThe clear solution is poured onto ice/water
  5. extractionis extracted with EA
  6. extractionextracted once more with EA
  7. dry with materialThe combined organic extracts are dried over Na2SO4
  8. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-a924afef2bb44fb7959946271415e80d
Source dataset
uspto-grants-2011_10
Patent number
US08039644B2

Reaction notes

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