Hydrochloric Acid → 54119-38-9

HRID 1619162Notes

Reaction equation

HRID 1619162 reaction equation
[CH3:1][Mg]Br.[CH3:4][C:5]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([CH3:15])=[CH:9][C:6]=1[CH:7]=[O:8].Cl>O1CCCC1.O>[CH3:14][O:13][C:11]1[C:10]([CH3:15])=[CH:9][C:6]([CH:7]([OH:8])[CH3:1])=[C:5]([CH3:4])[CH:12]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 812274-Methoxy-2,5-dimethylbenzaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 2113498354119-38-9Yield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl magnesium bromide (2.4 mL, 1.2 eq) was dropwise added at −78° C. to a solution of 2,5-dimethyl-4-methoxybenzaldehyde (1.0 g, 6.0 mmol) in 30 mL of tetrahydrofuran (THF) with stirring and the reaction mixture was allowed to react at that temperature while being stirred. After completion of the reaction, the reaction mixture was adjusted to pH 7 at 0° C. with 1N-HCl and concentrated in a vacuum. The residue thus obtained was stirred in water (20 mL) and extracted twice with 20 mL of dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtrated and concentrated in a vacuum to remove the solvent. The concentrate was purified through silica gel chromatography to yield 1-(4-methoxy-2,5-dimethylphenyl)ethanol as a white oil (0.87 g, yield 74%).

Workup

  1. customto react at that temperature
  2. stirringwhile being stirred
  3. customAfter completion of the reaction
  4. concentrationconcentrated in a vacuum
  5. customThe residue thus obtained
  6. extractionextracted twice with 20 mL of dichloromethane
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. filtrationfiltrated
  9. concentrationconcentrated in a vacuum
  10. customto remove the solvent
  11. customThe concentrate was purified through silica gel chromatography

Sources & evidence

ORD record
ord-a23889f68ac644da811aad3fbf6bb854
Source dataset
uspto-grants-2014_07
Patent number
US08772290B2

Reaction notes

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