P-Cresol → alpha-Hydroxy-beta-(4-Methylphenoxy)-N-(1-Methylethyl)Benzenepropanamide

HRID 435496Notes

Reaction equation

HRID 435496 reaction equation
[CH3:1][CH:2]([NH:4][C:5]([CH:7]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:8]1)=[O:6])[CH3:3].[CH:16]1[C:21]([OH:22])=[CH:20][CH:19]=[C:18]([CH3:23])[CH:17]=1.[H-].[Na+].C1OCCOCCOCCOCCOCCOC1>C(#N)C>[OH:8][CH:7]([CH:9]([O:22][C:21]1[CH:20]=[CH:19][C:18]([CH3:23])=[CH:17][CH:16]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:5]([NH:4][CH:2]([CH3:1])[CH3:3])=[O:6]

Participants

6

Reactant 4

HCID 2879P-CresolHCID 24758Sodium hydrideHCID 2855718-Crown-6HCID 13041334N-(1-methylethyl)-3-phenyl-2-oxiranecarboxamide

Product 1

HCID 13041340alpha-Hydroxy-beta-(4-Methylphenoxy)-N-(1-Methylethyl)Benzenepropanamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

This compound was prepared as in Example 12 from N-(1-methylethyl)-3-phenyl-2-oxiranecarboxamide (6.16 g.), p-cresol (3.3 g.), sodium hydride (50% oil dispersion, 1.5 g.), 18-crown-6 (0.9 g.) and acetonitrile (250 ml.). The product melted at 152°--152°, and amounted to 2.4 g.

Sources & evidence

ORD record
ord-a7cceb0f232244889c6066f6d74f4c4e
Source dataset
uspto-grants-1983_08
Patent number
US04401832

Reaction notes

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