Hydrochloric Acid → 1-(2-methoxyphenyl)-2-methylpropan-1-ol

HRID 2424308Notes

Reaction equation

HRID 2424308 reaction equation
O1C[CH2:4][CH2:3][CH2:2]1.[CH3:6][O:7][C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]=[O:11].C([Mg]Br)(C)C.Cl>O>[CH3:6][O:7][C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]([OH:11])[CH:3]([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 86582-MethoxybenzaldehydeHCID 178418365HCID 178418365, compound

Product 1

HCID 2258471-(2-methoxyphenyl)-2-methylpropan-1-olYield 74.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dry tetrahydrofuran (3 mL) was added to 1.01 g (7.43 mmol) of commercially available 2-methoxybenzaldehyde under nitrogen atmosphere, and the mixture was ice-cooled. To the mixture was added dropwise a 3.8 mL (7.6 mmol) of tetrahydrofuran solution containing 2 mol/L isopropylmagnesium bromide. After completion of dropwise addition, the reaction mixture was stirred in an ice bath for 1 hour. The reaction mixture was poured into water, made acidic with diluted hydrochloric acid, and then, extracted with ether. The organic layers were combined, washed successively with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed, and the obtained residue was purified by silica gel column chromatography (Wako gel C-100, hexane-ethyl acetate, gradient) to obtain 1.00 g (5.56 mmol, Yield: 74.8%) of 1-(2-methoxyphenyl)-2-methyl-1-propanol.

Workup

  1. temperaturecooled
  2. additionAfter completion of dropwise addition
  3. extractionextracted with ether
  4. washwashed successively with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed
  7. customthe obtained residue was purified by silica gel column chromatography (Wako gel C-100, hexane-ethyl acetate, gradient)

Sources & evidence

ORD record
ord-a6c1ddb0ec41478198e7689f66a37f80
Source dataset
uspto-grants-2011_06
Patent number
US07964531B2

Reaction notes

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