Dimethyl Sulfoxide → 2-(7-Methoxynaphthalen-1-yl)acetonitrile

HRID 2090565Notes

Reaction equation

HRID 2090565 reaction equation
Cl[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[CH:6]=[CH:5][CH:4]=1.CS(C)=O.O.[C-:20]#[N:21].[K+]>CC(OC)(C)C.O>[CH3:14][O:13][C:10]1[CH:11]=[C:12]2[C:7]([CH:6]=[CH:5][CH:4]=[C:3]2[CH2:2][C:20]#[N:21])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 9032Potassium CyanideHCID 199673051-(Chloromethyl)-7-methoxynaphthalene

Product 1

HCID 112640682-(7-Methoxynaphthalen-1-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 23212559water MeOtBuSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of the compound obtained in Step B (100 g) in 30 ml/g of DMSO and 5 ml/g of water there are added 1.2 equivalents of potassium cyanide (37.8 g). The reaction mixture is heated to 65° C. and maintained at 65° C. for 3 hours. After returning to ambient temperature, an MTBE/water (1/1) binary system is added to the mixture. The aqueous phase is removed. The organic phase is washed several times with water and then with saturated NaCl solution. The solvents are distilled off and the title compound is obtained in a quantitative yield.

Workup

  1. temperaturemaintained at 65° C. for 3 hours
  2. customAfter returning to ambient temperature
  3. customThe aqueous phase is removed
  4. washThe organic phase is washed several times with water
  5. distillationThe solvents are distilled off

Sources & evidence

ORD record
ord-4ebb4230462e4f0da21d9905b8dec6f3
Source dataset
uspto-grants-2013_05
Patent number
US08436206B2

Reaction notes

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