Hydrochloric Acid → 1-(1-Naphthyl)ethanol

HRID 1886526

Reaction equation

HRID 1886526 reaction equation
C[Mg]I.[Mg].[CH3:5]I.[C:7]1([CH:17]=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1.Cl>CCOCC>[C:7]1([CH:17]([OH:18])[CH3:5])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 61951-NaphthaldehydeHCID 6328Methyl iodideHCID 5462224MagnesiumHCID 178418373HCID 178418373, compound

Product 1

HCID 980301-(1-Naphthyl)ethanolYield 97.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a solution of methylmagnesium iodide in ether which was prepared from magnesium turning (1.08 g, 44.4 mmol) and methyl iodide (2.75 ml, 44.2 mmol) in 100 ml of ether, were added a solution of 1-naphthaldehyde (1) (5.75 g, 36.8 mmol) in 10 ml of ether with cooling in an ice-water bath, then the resulting reaction mixture was stirred for 2 hours at room temperature. To this mixture was added 25 ml of 2N hydrochloric acid and then the organic layer was separated from the aqueous layer. The organic layer was washed with 50 ml of brine and dried over sodium sulfate. Evaporation of the solvent in vacuo gave 6.20 g (97%) of 2 as a viscous oil.

Workup

  1. temperaturewith cooling in an ice-water bath
  2. customthe resulting reaction mixture
  3. customthe organic layer was separated from the aqueous layer
  4. washThe organic layer was washed with 50 ml of brine
  5. dry with materialdried over sodium sulfate
  6. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-a3da5b62b5fe4b86878a513d0376f67d
Source dataset
uspto-grants-1992_09
Patent number
US05151526

Linked notes

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