Phenol → alpha-Hydroxy-beta-Phenoxy-N-(1-Methylethyl)-4-Chlorobenzenepropanamide

HRID 435502Notes

Reaction equation

HRID 435502 reaction equation
[CH3:1][CH:2]([NH:4][C:5]([CH:7]1[CH:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[O:8]1)=[O:6])[CH3:3].[C:17]1([OH:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[H-].[Na+].C1OCCOCCOCCOCCOCCOC1>C(#N)C>[OH:8][CH:7]([CH:9]([O:23][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:10]1[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=1)[C:5]([NH:4][CH:2]([CH3:1])[CH3:3])=[O:6]

Participants

6

Reactant 4

HCID 996PhenolHCID 24758Sodium hydrideHCID 2855718-Crown-6HCID 13041336N-(1-methylethyl)-3-(4-chlorophenyl)-2-oxiranecarboxamide

Product 1

HCID 13041347alpha-Hydroxy-beta-Phenoxy-N-(1-Methylethyl)-4-Chlorobenzenepropanamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

This compound was prepared from N-(1-methylethyl)-3-(4-chlorophenyl)-2-oxiranecarboxamide (7.2 g.), phenol (3.0 g.), sodium hydride (50% oil dispersion, 1.6 g.), 18-crown-6 (0.9 g.), and acetonitrile (250 ml.) as described in Example 12. The crude product was recrystallized from ethanol, giving 2.3 g. of the compound, m.p. 175°-177°. Another recrystallization from ethanol gave analytical sample, m.p. 176°-178°.

Workup

  1. customThe crude product was recrystallized from ethanol
  2. customgiving 2.3 g
  3. customAnother recrystallization from ethanol
  4. customgave analytical sample, m.p. 176°-178°

Sources & evidence

ORD record
ord-0dc2efa9a2184257883d10c011c4190b
Source dataset
uspto-grants-1983_08
Patent number
US04401832

Reaction notes

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