Sodium Hydroxide → N,N-diisopropyl-3-phenyl-3-(2-hydroxy-5-methylphenyl)propionamide

HRID 2057165Notes

Reaction equation

HRID 2057165 reaction equation
[CH:1]([N:4]([CH:23]([CH3:25])[CH3:24])[C:5](=[O:22])[CH2:6][CH:7]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)OC1C=CC(C)=CC=1)([CH3:3])[CH3:2].[OH-:26].[Na+]>C1(C)C=CC=CC=1>[OH:26][C:19]1[CH:20]=[CH:21][C:16]([CH3:7])=[CH:17][C:18]=1[CH:7]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:6][C:5]([N:4]([CH:1]([CH3:2])[CH3:3])[CH:23]([CH3:24])[CH3:25])=[O:22]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11537400N,N-diisopropyl-3-phenyl-3-p-tolyloxy-propionamide

Product 1

HCID 11551832N,N-diisopropyl-3-phenyl-3-(2-hydroxy-5-methylphenyl)propionamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A three-necked round-bottom flask equipped with condenser, mechanical stirrer, thermometer, is loaded with N,N-diisopropyl-3-phenyl-3-p-tolyloxy-propionamide (1.0 g; 0.0029 mol) and polyphosphoric acid (16.5 g). After four hours under stirring at room temperature the reaction is completed. The reaction mixture is poured in ice/water (10 g), alkalinized to pH 9-10 with NaOH 50% w/w and left under stirring for 30 minutes, then diluted with toluene (30 ml). The phases are separated and the aqueous phase is extracted with toluene (2×30 ml). The combined organic phases are dried over sodium sulfate and evaporated to dryness. The resulting oil is purified by flash chromatography (hexane/ethyl acetate 7:3). 0.59 g of product, as a pale yellow oil, are obtained.

Workup

  1. customA three-necked round-bottom flask equipped with condenser, mechanical stirrer
  2. waitleft
  3. stirringunder stirring for 30 minutes
  4. customThe phases are separated
  5. extractionthe aqueous phase is extracted with toluene (2×30 ml)
  6. dry with materialThe combined organic phases are dried over sodium sulfate
  7. customevaporated to dryness
  8. customThe resulting oil is purified by flash chromatography (hexane/ethyl acetate 7:3)

Sources & evidence

ORD record
ord-28f10bfa74544994a1bd868e5550c852
Source dataset
uspto-grants-2008_02
Patent number
US07335793B2

Reaction notes

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