Sodium Hydroxide → HCID 19040962, compound

HRID 2209729Notes

Reaction equation

HRID 2209729 reaction equation
C([O:4][C:5]1[CH:19]=[C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][O:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][CH:28]=2)[CH:17]=[CH:16][C:6]=1[C:7]([N:9]([CH:13]([CH3:15])[CH3:14])[CH:10]([CH3:12])[CH3:11])=[O:8])(=O)C.[OH-].[Na+]>C(O)C>[C:33]([C:30]1[CH:29]=[CH:28][C:27]([O:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][O:20][C:18]2[CH:17]=[CH:16][C:6]([C:7]([N:9]([CH:13]([CH3:14])[CH3:15])[CH:10]([CH3:12])[CH3:11])=[O:8])=[C:5]([OH:4])[CH:19]=2)=[CH:32][CH:31]=1)#[N:34]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15295289HCID 15295289, compound

Product 1

HCID 19040962HCID 19040962, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 2-acetoxy-4-[5-(4-cyanophenoxy)pentyloxy]-N,N-bis(1-methylethyl)benzamide (10 g, 21.5 mmol) in 250 mL of ethanol is treated with 1N sodium hydroxide solution (25 mL, 25 mmol). After stirring at room temperature for 2 hours, the reaction is concentrated in vacuo. This material is partitioned between ethyl acetate and 1N hydrochloric acid. The organic phase is washed with brine, dried over sodium sulfate, and concentrated in vacuo. The resulting material is purified by chromatography on silica gel (200 g) with 40-50% ethyl acetate/hexane as the eluent to afford 4-[5-(4-cyanophenoxy)pentyloxy]-2-hydroxy-N,N-bis(1-methylethyl)benzamide as a colorless foam.

Workup

  1. concentrationthe reaction is concentrated in vacuo
  2. customThis material is partitioned between ethyl acetate and 1N hydrochloric acid
  3. washThe organic phase is washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting material is purified by chromatography on silica gel (200 g) with 40-50% ethyl acetate/hexane as the eluent

Sources & evidence

ORD record
ord-1487c1d481424846b81a6c7a1c3dcc87
Source dataset
uspto-grants-1995_10
Patent number
US05455274

Reaction notes

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