Sodium Hydroxide → HCID 12898556, compound

HRID 2050069Notes

Reaction equation

HRID 2050069 reaction equation
[CH2:1]([NH:8][C:9](=O)[CH2:10][O:11][C:12]1[C:17]([CH3:18])=[CH:16][C:15]([C:19]([OH:28])([C:24]([F:27])([F:26])[F:25])[C:20]([F:23])([F:22])[F:21])=[CH:14][C:13]=1[CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[H-].[H-].[OH-].[Na+]>C1(C)C=CC=CC=1>[F:21][C:20]([F:22])([F:23])[C:19]([C:15]1[CH:14]=[C:13]([CH3:29])[C:12]([O:11][CH2:10][CH2:9][NH:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:17]([CH3:18])[CH:16]=1)([OH:28])[C:24]([F:25])([F:27])[F:26]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 12898553HCID 12898553, compoundHCID 21584524Aluminiumhydride

Product 1

HCID 12898556HCID 12898556, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To N-benzyl-2-[4-(hexafluoro-2-hydroxy-2-propyl)-2,6-dimethylphenoxy]acetamide (3.0 g=6.0 mmol) in 75 ml toluene add sodium bis-2-methoxyethoxy)aluminum hydride (70% solution in benzene, 8.0 g=28 mmol) over 1/2 hour. Stir 16 hours, treat with 1.0 N NaOH, and extract with ethyl acetate. Dry and concentrate the organic layer. Recrystallize from ether-hexane to give 2-[4-(hexafluoro-2-hydroxy-2-propyl)-2,6-dimethylphenoxy]ethylbenzylamine, as white crystals, m.p. 117°-120° C.

Workup

  1. extractionextract with ethyl acetate
  2. customDry
  3. concentrationconcentrate the organic layer
  4. customRecrystallize from ether-hexane

Sources & evidence

ORD record
ord-6220bfd014f94d78986b1bfaa6142fec
Source dataset
uspto-grants-1980_04
Patent number
US04199597

Reaction notes

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