Sulfuric Acid → HCID 85840824, compound

HRID 2352658Notes

Reaction equation

HRID 2352658 reaction equation
O=[C:2]([CH3:15])[CH2:3][CH2:4][CH:5]1[C:10]([CH3:12])([CH3:11])[CH2:9][CH2:8][C:7](=[O:13])[CH:6]1[CH3:14].S(=O)(=O)(O)O.S([O-])([O-])(=O)=O.[NH4+].[NH4+]>C(OCC)(=O)C.C(OCC)C.O.[C].[Pd]>[CH3:15][C:2]1[C:6]2([CH3:14])[CH:5]([C:10]([CH3:12])([CH3:11])[CH2:9][CH2:8][C:7]2=[O:13])[CH2:4][CH:3]=1

Participants

8

Reactant 3

HCID 1118Sulfuric Acid2×HCID 6097028Ammonium SulfateHCID 19843686HCID 19843686, compound

Product 1

HCID 85840824HCID 85840824, compoundYield 83.8%

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

60 g of 3-(3-oxobutyl)-2,4,4-trimethyl-cyclohexanone (product of the catalytic hydrogenation of 4-ketoionone with palladium-carbon in ethyl acetate at room temperature and normal pressure, see H. Jwamuro et al., 23rd Proceedings of the Chemical Society of Japan, 86 [1979]) are dissolved in 500 ml of diethyl ether and at the reflux temperature of the solution there are immediately added dropwise while stirring 25 ml of 80% sulphuric acid. A further 25 ml of 80% sulphuric acid are added dropwise four times after a reaction time of 1 hour in each case. 30 minutes after the last addition of the brownish reaction mmixture is poured onto ice, diluted with water to about 1.5 l, the emulsion is broken with ammonium sulphate and the aqueous phase is separated. After washing with sodium bicarbonate solution and water the organic phase is dried as usual and evaporated under a vacuum. After flat distillation at 55°-60° C./0.05 Torr there are obtained 46 g of 1,4,4,7a-tetramethyl-3a,4,5,7a-tetrahydro-7(6H)-ind-1-enone.

Workup

  1. customat room temperature
  2. additionthere are immediately added dropwise
  3. addition30 minutes after the last addition of the brownish reaction mmixture
  4. additionis poured onto ice
  5. customthe aqueous phase is separated
  6. washAfter washing with sodium bicarbonate solution and water the organic phase
  7. customis dried as usual and
  8. customevaporated under a vacuum
  9. distillationAfter flat distillation at 55°-60° C./0.05 Torr there

Sources & evidence

ORD record
ord-c4b362eff09b4ff3bf9da67fca262842
Source dataset
uspto-grants-1989_10
Patent number
US04877904

Reaction notes

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