Sodium Cyanide → 1-Naphthalenecarbonitrile, 3,4-dihydro-6-methoxy-

HRID 280483Notes

Reaction equation

HRID 280483 reaction equation
[C-:1]#[N:2].[Na+].[CH3:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=O)[CH2:11][CH2:10][CH2:9]2.[Al+3].[Cl-].[Cl-].[Cl-]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.[N+](C1C=CC=CC=1)([O-])=O>[CH3:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12]([C:1]#[N:2])=[CH:11][CH2:10][CH2:9]2

Participants

6

Reactant 3

HCID 8929Sodium Cyanide2×HCID 141126-Methoxy-alpha-tetralone3×HCID 6451240Aluminum(III) Chloride

Product 1

HCID 30144661-Naphthalenecarbonitrile, 3,4-dihydro-6-methoxy-

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalyst2×HCID 7416NitrobenzeneSolvent

Procedure

A mixture of 1.3 g of dry AlCl 3, 0.64 g of dry NaCN, and 87 mg of tetrabutylammonium bromide (TBAB) in 8.7 ml of dry nitrobenzene (NB) was stirred for two hours under a nitrogen atmosphere. Then 1.53 g of 6-methoxytetralone (6-MT) were added to provide a reaction mixture containing the 6-MT, NaCN, and AlCl3 in a mol ratio of 1/1.5/1.1 and containing 5.6% of TBAB, based on the weight of 6-MT. The reaction mixture was stirred at 90° C. for 10 hours to form 6-methoxy-1-cyano-3,4-dihydronaphthalene (6-MCDN). After workup the VPC ratio of 6-MT/6-MCDN was determined to be 8/92. The process resulted in an 85% isolated yield of 6-MCDN.

Workup

  1. customto provide a reaction mixture
  2. stirringThe reaction mixture was stirred at 90° C. for 10 hours

Sources & evidence

ORD record
ord-c368c7455dfa4e40b467d0655a122c1e
Source dataset
uspto-grants-1986_05
Patent number
US04590010

Reaction notes

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