Phosphorus oxychloride → 5-Methoxy-3,4-dihydronaphthalene-1-carbonitrile

HRID 2290913Notes

Reaction equation

HRID 2290913 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=O.[Si]([C:18]#[N:19])(C)(C)C.[Al+3].[Cl-].[Cl-].[Cl-].O=P(Cl)(Cl)Cl>N1C=CC=CC=1.C1C=CC=CC=1>[C:18]([C:8]1[C:9]2[C:4](=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:6][CH:7]=1)#[N:19]

Participants

7

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 366205-MethoxytetraloneHCID 82115Trimethylsilyl cyanideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 150299205-Methoxy-3,4-dihydronaphthalene-1-carbonitrile

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1049PyridineSolvent

Procedure

A solution of 5-methoxy-1-tetralone (52.0 g, 0.29 mole, Aldrich), TMSCN (51 mL, 0.38 mole, Aldrich), 40 mL dry benzene, and catalytic AlCl3 was stirred under N2 at 65° C. for 1 hour. The reaction mixture was cooled and evaporated to dryness. To the residue was added 300 mL pyridine and POCl3 (80 mL, 0.88 mole). The reaction mixture was stirred at reflux for 2 hours, then was cooled to room temperature and was poured onto ice/concentrated HCl. A precipitate was collected, washed with water, and purified by column chromatography (silica gel/CH2Cl2) to obtain 54 g (73%); M+ 185.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customevaporated to dryness
  3. temperatureat reflux for 2 hours
  4. additionwas poured onto ice/concentrated HCl
  5. customA precipitate was collected
  6. washwashed with water
  7. custompurified by column chromatography (silica gel/CH2Cl2)
  8. customto obtain 54 g (73%)

Sources & evidence

ORD record
ord-df39daaff75648d0997e68052dfd8236
Source dataset
uspto-grants-1986_10
Patent number
US04618683

Reaction notes

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