HCID 19606262, compound → HCID 19606353, compound

HRID 1603908Notes

Reaction equation

HRID 1603908 reaction equation
C([O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([Cl:13])[CH:6]=1)C=C.[CH2:14]([C:17]1C(O)=CC(Cl)=C(C=1)C#N)[CH:15]=C>>[CH2:17]([C:6]1[C:7]([Cl:13])=[C:8]([CH:11]=[CH:12][C:5]=1[OH:4])[C:9]#[N:10])[CH:14]=[CH2:15]

Participants

3

Reactant 2

HCID 19606262HCID 19606262, compoundHCID 19606284HCID 19606284, compound

Product 1

HCID 19606353HCID 19606353, compoundYield 51%

Procedure

Following the process described in example 6 (point B), starting from 4-allyloxy-2-chlorobenzonitrile, a mixture of 5-allyl-2-chloro-4-hydroxybenzonitrile and 3-allyl-2-chloro-4-hydroxybenzonitrile was obtained. The two isomers were separated by chromatography through a silica gel column. Eluting with petroleum ether:ethyl ether, 8:2, the isomer 5-allyl-2-chloro-4-hydroxybenzonitrile (39% yield) was recovered and eluting with petroleum ether:ethyl ether, 6:4, the isomer 3-allyl-2-chloro-4-hydroxybenzonitrile was recovered (51% yield).

Sources & evidence

ORD record
ord-3ca028420c0a4ad388f5f732135ed556
Source dataset
uspto-grants-1999_11
Patent number
US05990142

Reaction notes

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