Hydrochloric Acid → 4-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-2-butanone

HRID 2199011Notes

Reaction equation

HRID 2199011 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:16])([CH3:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:4][C:3]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Mg].[CH:26]([C:28]([CH3:30])=[O:29])=[CH2:27].Cl>O1CCCC1>[CH2:18]([O:17][C:3]1[CH:4]=[C:5]([C:8]([CH3:16])([CH3:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:6]=[CH:7][C:2]=1[CH2:27][CH2:26][C:28](=[O:29])[CH3:30])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6570Methyl vinyl ketoneHCID 5462224MagnesiumHCID 128821642-(Benzyloxy)-1-bromo-4-(2-methyloctan-2-YL)benzene

Product 1

HCID 128821654-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-2-butanoneYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

A solution of 3.89 g. (0.010 mol.) of 1-bromo-2-benzyloxy-4-(1,1-dimethylheptyl)benzene in 15 ml. of tetrahydrofuran was slowly added to 0.36 g. (0.015 mol.) of 70-80 mesh magnesium metal. The resultant mixture was refluxed for 20 minutes and was then cooled to -10° C. Cuprous iodide (0.115 g., 0.006 mol.) was added and stirring continued for 10 minutes. To the resultant mixture was slowly added a solution of 0.701 g. (0.010 ml.) of metyl vinyl ketone in 5 ml. of tetrahydrofuran at such a rate that the reaction temperature could be maintained below 0° C. The reaction mixture was stirred for 30 minutes longer (t<0° C.) and then added to 100 ml. of 1 N hydrochloric acid and 100 g. of ice. The quenched reaction was extracted three times with 150 ml. portions of ether. The combined ether extract was washed twice with 100 ml. portions of water, twice with 100 ml. portions of saturated sodium chloride, dried over magnesium sulfate and evaporated to an oil. The oil was purified via column chromatography on 180 g. of silica gel eluted with 20% ether-cyclohexane to yield 1.07 g. (28%) of the title compound as an oil.

Workup

  1. stirringThe reaction mixture was stirred for 30 minutes longer (t<0° C.)
  2. additionadded to 100 ml
  3. customThe quenched reaction
  4. extractionwas extracted three times with 150 ml
  5. extractionThe combined ether extract
  6. washwas washed twice with 100 ml
  7. dry with materialportions of saturated sodium chloride, dried over magnesium sulfate
  8. customevaporated to an oil
  9. customThe oil was purified via column chromatography on 180 g
  10. washof silica gel eluted with 20% ether-cyclohexane
  11. customto yield 1.07 g

Sources & evidence

ORD record
ord-b4d8ff7df6184bfe9ad2b7449032e48e
Source dataset
uspto-grants-1982_11
Patent number
US04360700

Reaction notes

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