Acetone → HCID 13188177, compound

HRID 851329Notes

Reaction equation

HRID 851329 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1([CH3:23])[CH2:18][CH2:17][CH2:16][CH2:15][C:14]21OCC[O:19]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=O.OS(O)(=O)=O>O>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1([CH3:23])[CH2:18][CH2:17][CH2:16][CH2:15][C:14]1=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 13188176HCID 13188176, compound

Product 1

HCID 13188177HCID 13188177, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the 2-(4'-benzyloxybutyl)-1,1-ethylenedioxy-2-methylcyclohexane (32.5 g, 0.10 mol), acetone (375 ml), H2O (50 ml) and 0.002 N H2SO4 (125 ml) is refluxed for 18 hours under a nitrogen atmosphere. The reaction mixture is cooled, the acetone is evaporated under reduced pressue and the aqueous layer extracted with ether (3×500 ml). The combined organic layers are washed with satd. NaHCO3 (2×300 ml), satd. NaCl (2×500 ml) and dried (MgSO4). The solvents are removed under reduced pressure and the crude product (29 g) is chromatographed on SilicAR CC-7 (500 g) in hexane. Elution with 5% ethyl acetate/hexane gives 2-(4'-benzyloxybutyl)-2-methylcyclohexanone as a colorless oil (25.4 g, 91%): ir (neat) 1705 cm-1 (CO); nmr (CDCl3) δ1.03 (s, 3H, CH3), 2.35 (m, 2H, OC-- CH2 --CH2), 3.5 (t, 2H, O--CH2 --CH2), 4.44 (s, 2H, O--CH2 --Ph), 7.3 (s, 5H, aromatic).

Workup

  1. temperatureis refluxed for 18 hours under a nitrogen atmosphere
  2. temperatureThe reaction mixture is cooled
  3. customthe acetone is evaporated under reduced pressue
  4. extractionthe aqueous layer extracted with ether (3×500 ml)
  5. washThe combined organic layers are washed with satd
  6. dry with materialNaCl (2×500 ml) and dried (MgSO4)
  7. customThe solvents are removed under reduced pressure
  8. customthe crude product (29 g) is chromatographed on SilicAR CC-7 (500 g) in hexane
  9. washElution with 5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-a5a131249ca04dc580b688bab22bc535
Source dataset
uspto-grants-1983_05
Patent number
US04384126

Reaction notes

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