Hydrochloric Acid → 2-(Benzyloxy)-4-ethylphenol

HRID 1023895Notes

Reaction equation

HRID 1023895 reaction equation
C[O:2]S(C1C=CC=CC=1)(=O)=O.[CH2:12]([O:19][C:20]1[CH:25]=[C:24]([CH2:26][CH3:27])[CH:23]=[CH:22][C:21]=1C1C=C(C)C=CC=1S(O)(=O)=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Mg].Cl>CO>[CH2:12]([O:19][C:20]1[CH:25]=[C:24]([CH2:26][CH3:27])[CH:23]=[CH:22][C:21]=1[OH:2])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5462224MagnesiumHCID 866390952-(Benzyloxy)-4-ethylphenyl-4-methylbenzenesulfonate methylbenzenesulfonate

Product 1

HCID 591912432-(Benzyloxy)-4-ethylphenolYield 80.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(benzyloxy)-4-ethylphenyl-4-methylbenzenesulfonate methylbenzenesulfonate (0.26 mmol; 100 mg) under argon, in methanol (2 mL), was added magnesium (2.61 mmol; 0.63 g). The reaction was stirred at room temperature overnight. The reaction mixture was hydrolysed with HCl 1N (3 mL) and extracted with ethyl acetate (3*5 mL). Combined organic phases were washed with saturated NaHCO3 (10 mL), dried over Na2SO4, concentrated. The residue was purified with preparative TLC (dichloromethane/cyclohexane: 9/1) to yield the title compound as a yellow oil (48 mg; 0.21 mmol; 80%).

Workup

  1. extractionextracted with ethyl acetate (3*5 mL)
  2. washCombined organic phases were washed with saturated NaHCO3 (10 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified with preparative TLC (dichloromethane/cyclohexane: 9/1)

Sources & evidence

ORD record
ord-e3ed72eb42be48ffb46f5cf33f5e31a4
Source dataset
uspto-grants-2014_05
Patent number
US08722746B2

Reaction notes

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