Hexane → 1-(3-Benzyloxyphenyl)-1,1-dimethylheptane

HRID 894966Notes

Reaction equation

HRID 894966 reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH3:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[CH2:15]([O:22][C:23]1[CH:24]=[C:25]([C:29](Cl)([CH3:31])[CH3:30])[CH:26]=[CH:27][CH:28]=1)C1C=CC=CC=1.[Cl-].[NH4+]>CCOCC>[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([CH3:30])([CH3:31])[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH:24]=1)[C:11]1[CH:10]=[CH:9][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 8058Hexane2×HCID 25517Ammonium ChlorideHCID 133680332-(3-Benzyloxyphenyl)-2-chloropropaneHCID 178444609HCID 178444609, compound

Product 1

HCID 130526961-(3-Benzyloxyphenyl)-1,1-dimethylheptaneYield 35%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a 0° C. mixture of 10.1 mmole of n-hexyl magnesium bromide in 5 ml. of hexane is added dropwise a solution of 2.0 g. (7.69 mmole) of 2-(3-benzyloxyphenyl)-2-chloropropane in 14 ml. of hexane. The reaction mixture is stirred 5 minutes longer and then added to 500 ml. of saturated ammonium chloride and 300 ml. ether. The organic extract is dried over magnesium sulfate and evaporated to an oil. The oil is purified via column chromatography on 150 g. of silica gel eluted with hexane to yield 841 mg. (35%) of the title compound as an oil.

Workup

  1. additionadded to 500 ml
  2. extractionThe organic extract
  3. dry with materialis dried over magnesium sulfate
  4. customevaporated to an oil
  5. customThe oil is purified via column chromatography on 150 g
  6. washof silica gel eluted with hexane
  7. customto yield 841 mg

Sources & evidence

ORD record
ord-9957554eef6d4d9b8c5aa28931435b6a
Source dataset
uspto-grants-1981_08
Patent number
US04285867

Reaction notes

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