Ethanol → 2-Methyl-1-naphthaleneacetonitrile

HRID 1814286Notes

Reaction equation

HRID 1814286 reaction equation
Cl[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[CH3:13].[C-:14]#[N:15].[K+].CCO>O>[CH3:13][C:4]1[CH:5]=[CH:6][C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:2][C:14]#[N:15]

Participants

5

Reactant 3

HCID 702EthanolHCID 9032Potassium CyanideHCID 811061-Chloromethyl-2-methylnaphthalene

Product 1

HCID 1122982-Methyl-1-naphthaleneacetonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

1-Chloromethyl-2-methylnaphthalene (5.00 g, 26.3 mmol) and KCN (5.12 g, 78.8 mmol) were combined in H2O (20 mL) and EtOH (40 mL) in a round bottom flask fitted with a reflux condenser. The mix was stirred at 80° C. for 18 hours. TLC analysis (silica, 10% acetone-hexanes) indicated consumption of the starting chloromethylnaphthalene. The reaction was allowed to cool to room temperature and then was diluted with H2O. The dilution was extracted three times with EtOAc. The organic extracts were combined, washed with brine solution, dried over Na2SO4, decanted, and concentrated to give (2-methyl-naphthalen-1-yl)-acetonitrile in quantitative yield. MS (APCI) m/z 180.1 (M−H). 1H NMR (400 MHz) CDCl3 δ 7.96 (d, J=8.4 Hz, 1H), 7.85 (d, J=8.2 Hz, 1H), 7.77 (d, J=8.4 Hz, 1H), 7.61 (m ,1H), 7.50 (m, 1H), 7.34 (d, J=8.4, 1H), 4.07 (s, 2H), 2.58 (s, 3H).

Workup

  1. customconsumption of the starting chloromethylnaphthalene
  2. temperatureto cool to room temperature
  3. additionwas diluted with H2O
  4. extractionThe dilution was extracted three times with EtOAc
  5. washwashed with brine solution
  6. dry with materialdried over Na2SO4
  7. customdecanted
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3b46794732bb4799a8df080a8109245a
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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