O-Cresol → alpha-Hydroxy-beta-(2-Methylphenoxy)-N-(1-Methylethyl)Benzenepropanamide

HRID 435498Notes

Reaction equation

HRID 435498 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].[C:16]1([CH3:23])[C:21]([OH:22])=[CH:20][CH:19]=[CH:18][CH:17]=1.[H-].[Na+].C1OCCOCCOCCOCCOCCOC1>C(#N)C>[OH:8][CH:7]([CH:9]([O:22][C:21]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:23])[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 335O-CresolHCID 24758Sodium hydrideHCID 2855718-Crown-6HCID 13041334N-(1-methylethyl)-3-phenyl-2-oxiranecarboxamide

Product 1

HCID 13041342alpha-Hydroxy-beta-(2-Methylphenoxy)-N-(1-Methylethyl)Benzenepropanamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

This compound was prepared from N-(1-methylethyl)-3-phenyl-2-oxiranecarboxamide (8.2 g.) o-cresol (4.3 g.), sodium hydride (50% oil dispersion, 1.9 g.), 18-crown-6 (1.0 g.), and acetonitrile (250 ml.) as described in Example 12. The compound after recrystallization from ether melted at 123°-124°, and weighed 1.25 g.

Workup

  1. customThe compound after recrystallization from ether melted at 123°-124°

Sources & evidence

ORD record
ord-a1bb3436e102452e9c45818abfd6b1f7
Source dataset
uspto-grants-1983_08
Patent number
US04401832

Reaction notes

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