Water → 4-(3-Cyanopropyl)-6-methoxy-1,2-dihydronaphthalene

HRID 582199Notes

Reaction equation

HRID 582199 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[CH2:8][CH2:7][CH:6]=1.[C-:17]#[N:18].[Na+].O>CS(C)=O>[CH3:16][O:15][C:12]1[CH:13]=[C:14]2[C:9]([CH2:8][CH2:7][CH:6]=[C:5]2[CH2:4][CH2:3][CH2:2][C:17]#[N:18])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 104238234-(3-Bromopropyl)-6-methoxy-1,2-dihydronaphthalene

Product 1

HCID 219964624-(3-Cyanopropyl)-6-methoxy-1,2-dihydronaphthaleneYield 93%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 4-(3-bromopropyl)-1,2-dihydro-6-methoxynaphthalene (10 g, 35.6 mmol.) and sodium cyanide (1.92 g, 39.1 mmol.) was stirred in dimethyl sulfoxide (20 ml) for one hour at room temperature. The reaction mixture was poured into water, then the organic substance was extracted with ethyl acetate. The extract solution was washed with a saturated aqueous saline solution and water, which was dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue thus obtained was purified by means of a silica gel column chromatography (ethyl acetate:hexane=1:9) to afford the titled compound. (7.5 g, yield 93%, oily).

Workup

  1. extractionthe organic substance was extracted with ethyl acetate
  2. washThe extract solution was washed with a saturated aqueous saline solution and water, which
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. distillationby distilling off the solvent under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by means of a silica gel column chromatography (ethyl acetate:hexane=1:9)

Sources & evidence

ORD record
ord-381b895364f1406bba7b3387d796e5b0
Source dataset
uspto-grants-1999_07
Patent number
US05922771

Reaction notes

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