Hydrochloric Acid → 2-(3,3-Dimethylbutyl)phenyl-1-ethanone

HRID 1596819Notes

Reaction equation

HRID 1596819 reaction equation
C(N=[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:10])C1C=CC=CC=1.[CH3:17][C:18]([CH3:22])([CH3:21])[CH:19]=[CH2:20].Cl.C1C[O:27]CC1>C1(C)C=CC=CC=1>[CH3:17][C:18]([CH3:22])([CH3:21])[CH2:19][CH2:20][C:16]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:9](=[O:27])[CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 112103,3-Dimethyl-1-buteneHCID 297338N-benzyl-1-phenylethanimine

Product 1

HCID 114470522-(3,3-Dimethylbutyl)phenyl-1-ethanoneYield 97%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

In a 500 ml pressure reactor, N-benzyl-(1-phenylethylidene)-amine 68 mg (0.32 mmol), tristriphenylphosphine rhodium (I) chloride 6 mg (0.0065 mmol), 3,3-dimethyl-1-butene 27 mg (0.32 mmol) were placed and dissolved in toluene 100 mg. While the reactor was stopped with a stopper, the reactants were heated at 150° C. for 2 hours with stirring. After completion of the reaction, the reactant mixture was dissolved in THF 3 ml and then combined with 1 N HCl soln. 10 ml, followed by hydrolysis with stirring for 12 hours at room temperature. After the mixture was three times extracted with Et2O and CH2Cl2, the organic layer was dried over MgSO4 and then filtered and the solvent was evaporated under reduced pressure. The reactant mixture of the organic layer was purified by column chromatography on silica gel (5:2 hexane:ethyl acetate) to obtain 2-(3,3-dimethylbutyl)phenyl-1-ethanone 64 mg (0.31 mmol). Yield: 97%. Under the same conditions, a variety of olefins were employed, and the results are given in Table 1, below.

Workup

  1. customAfter completion of the reaction
  2. custom10 ml, followed by hydrolysis
  3. stirringwith stirring for 12 hours at room temperature
  4. extractionextracted with Et2O and CH2Cl2
  5. dry with materialthe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure
  8. additionThe reactant mixture of the organic layer
  9. customwas purified by column chromatography on silica gel (5:2 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-00a4da29588c48dcb6e5ece31b48f3e0
Source dataset
uspto-grants-2001_09
Patent number
US06291716B1

Reaction notes

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