Butyl nitrite → HCID 6813148, compound

HRID 1719492Notes

Reaction equation

HRID 1719492 reaction equation
[CH3:1][O:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]1=[O:13].CCCC[O:18][N:19]=O.[O-:21]CC.[K+]>>[OH:18][N:19]=[C:7]1[CH2:8][CH2:9][C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)[C:6]1=[O:21].[OH:18][N:19]=[C:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]1=[O:13]

Participants

5

Reactant 3

HCID 10996Butyl nitriteHCID 110951552-Methoxy-3,4-dihydronaphthalen-1(2H)-one2×HCID 23670592Potassium ethoxide

Product 2

HCID 6813148HCID 6813148, compoundHCID 73667394HCID 73667394, compound

Procedure

4-(p-methoxyphenyl)butanoic acid (Compound 13, R1 =H, R2 =CH3) is treated with polyphosphoric acid (PPA) to form 7-methoxytetralone via Friedel-Crafts acylation (Compound 1, R1 =H, R2 =CH3 on C7. ##STR19## The tetralone (Compound 1) is then reacted with N-butylnitrite and potassium ethoxide to yield 2-hydroxyimino-7-methoxy-1-tetralone (Compound 2, R2 =CH3 on C7.

Sources & evidence

ORD record
ord-781c90d0092544a3b8cd4f8ea46c9e91
Source dataset
uspto-grants-1985_09
Patent number
US04540691

Reaction notes

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