1-Butanol → 2-(2,5-Dimethylphenoxymethyl)-alpha-methoxyiminophenylacetic acid

HRID 1720563Notes

Reaction equation

HRID 1720563 reaction equation
[CH3:1][C:2]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:3]=1[O:4][CH2:5][C:6]1[CH:17]=[CH:16][CH:15]=[CH:14][C:7]=1[C:8]([C:12]#N)=[N:9][O:10][CH3:11].[OH-:23].[K+].C(O)CCC.Cl.[OH2:31]>>[CH3:1][C:2]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:3]=1[O:4][CH2:5][C:6]1[CH:17]=[CH:16][CH:15]=[CH:14][C:7]=1[C:8](=[N:9][O:10][CH3:11])[C:12]([OH:31])=[O:23]

Participants

6

Reactant 5

HCID 2631-ButanolHCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 54390956HCID 54390956, compound

Product 1

HCID 543974242-(2,5-Dimethylphenoxymethyl)-alpha-methoxyiminophenylacetic acidYield 95.5%

Procedure

To 2-(2,5-dimethylphenoxymethyl)-α-methoxyiminobenzyl cyanide (E/Z=13/87)(2.94 g, 10 mmol) were added 96.7% potassium hydroxide (1.16 g, 20 mmol), butanol (20 ml) and water (2 ml). The mixture was stirred under reflux for 13 hours. After completion of the reaction, 1N aqueous hydrochloric acid solution (150 ml) was added. The mixture was extracted with toluene (150 ml), washed with water (100 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give crude 2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxyiminoacetic acid (2.99 g, Yield 95.5%, Z=at least 99%).

Workup

  1. temperatureunder reflux for 13 hours
  2. additionwas added
  3. extractionThe mixture was extracted with toluene (150 ml)
  4. washwashed with water (100 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a1285e0b37e24328b2afc37e097d7203
Source dataset
uspto-grants-1996_04
Patent number
US05506358

Reaction notes

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