3,5-Dimethyl-4-hydroxybenzonitrile → HCID 136034837, compound

HRID 1681916Notes

Reaction equation

HRID 1681916 reaction equation
[CH3:1][C:2]1C=C(C=[C:8](C)[C:9]=1O)C#N.[CH3:12][O:13][C:14]1[C:19]([CH3:20])=[C:18]([O:21][CH3:22])[CH:17]=[CH:16][C:15]=1[C:23]1[N:27]=[C:26]([CH3:28])[O:25][N:24]=1>>[C:2]([CH2:9][CH2:8][CH2:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([C:23]2[N:27]=[C:26]([CH3:28])[O:25][N:24]=2)=[C:14]([OH:13])[C:19]=1[CH3:20])#[CH:1].[C:2]([CH2:9][CH2:8][CH2:12][O:13][C:14]1[C:19]([CH3:20])=[C:18]([OH:21])[CH:17]=[CH:16][C:15]=1[C:23]1[N:27]=[C:26]([CH3:28])[O:25][N:24]=1)#[CH:1]

Participants

4

Reactant 2

HCID 201763,5-Dimethyl-4-hydroxybenzonitrileHCID 19804358HCID 19804358, compound

Product 2

HCID 136034837HCID 136034837, compoundHCID 136150977HCID 136150977, compound

Procedure

By following a procedure similar to that described in Example 1(a) but substituting for the 3,5-dimethyl-4-hydroxybenzonitrile an equimolar amount of the compound from Example 8, part (d), there can be obtained 3-[4-(3-ethinylpropoxy)-2-hydroxy-3-methylphenyl]-5-methyl-1,2,4-oxadiazole and its positional isomer 3-[2-(3-ethinylpropoxy)-4-hydroxy-3-methylphenyl]-5-methyl-1,2,4-oxadiazole which can be separated by conventional procedures.

Sources & evidence

ORD record
ord-024fb3feec084884a0845add1bc27a80
Source dataset
uspto-grants-1992_12
Patent number
US05175177

Reaction notes

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