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

HRID 280481

Reaktionsgleichung

Reaktionsgleichung von HRID 280481
[Al+3].[Cl-].[Cl-].[Cl-].[C-:5]#[N:6].[Na+].[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[C:16](=O)[CH2:15][CH2:14][CH2:13]2>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.[N+](C1C=CC=CC=1)([O-])=O>[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[C:16]([C:5]#[N:6])=[CH:15][CH2:14][CH2:13]2

Komponenten

6

Edukt 3

HCID 8929Sodium Cyanide2×HCID 141126-Methoxy-alpha-tetralone3×HCID 6451240Aluminum(III) Chloride2×

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysator2×HCID 7416NitrobenzeneLösungsmittel

Versuchsvorschrift

A mixture of 1.3 g of dry AlCl3, 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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-df20106b82b74b4592ec466c6d7cc949
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04590012

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