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

HRID 280486Notes

Reaction equation

HRID 280486 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=O)[CH2:8][CH2:7][CH2:6]2.[C-:14]#[N:15]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:14]#[N:15])=[CH:8][CH2:7][CH2:6]2

Participants

3

Reactant 2

HCID 5975CyanideHCID 141126-Methoxy-alpha-tetralone

Product 1

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

Procedure

The process of claim 1 wherein (1) 6-methoxytetralone is reacted with cyanide ion and a Lewis acid so as to form 6-methoxy-1-cyano-3,4-dihydronaphthalene, (2) the 6-methoxy-1-cyano3,4-dihydronaphthalene is dehydrogenated to 6-methoxy-1-cyanonaphthalene, (3) the 6-methoxy-1-cyanonaphthalene is halogenated so as to form a 6-methoxy-5-halo-1-cyanonaphthalene and then trifluoromethylated to replace the halo substituent with a trifluoromethyl group, and (4) the resultant 6-methoxy-5-trifluoromethyl-1-cyanonaphthalene is hydrolyzed to 6-methoxy-5-trifluoromethyl-1-naphthoic acid.

Sources & evidence

ORD record
ord-f660d14ce74549ac8a35c739f28c7fba
Source dataset
uspto-grants-1986_05
Patent number
US04590010

Reaction notes

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