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

HRID 894417Notes

Reaction equation

HRID 894417 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 is slowly added to 0.36 g. (0.015 mol.) of 70-80 mesh magnesium metal. The resultant mixture is refluxed for 20 minutes and is then cooled to -10° C. Cuprous iodide (0.115 g., 0.006 mol.) is added and stirring continued for 10 minutes. To the resultant mixture is slowly added a solution of 0.701 g. (0.010 mol.) of methyl vinyl ketone in 5 ml. of tetrahydrofuran at such a rate that the reaction temperature could be maintained below 0° C. The reaction mixture is stirred for 30 minutes longer (t<0° C.) and is then added to 100 ml. of 1 N hydrochloric acid and 100 g. of ice. The quenched reaction is extracted three times with 150 ml. portions of ether. The combined ether extract is 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 is stirred for 30 minutes longer (t<0° C.)
  2. additionis then added to 100 ml
  3. customThe quenched reaction
  4. extractionis extracted three times with 150 ml
  5. extractionThe combined ether extract
  6. washis 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-d542736627ed461ea248a7dc2a3aa37f
Source dataset
uspto-grants-1981_08
Patent number
US04283569

Reaction notes

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