Hydrochloric Acid → 2-(4-Octyloxyphenyl)-2-methoxyiminoacetic acid

HRID 1492900Notes

Reaction equation

HRID 1492900 reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=O)[C:17]([OH:19])=[O:18])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Cl.Cl.[CH3:23][O:24][NH2:25].C(OCC)(=O)C>O.O1CCCC1>[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[N:25][O:24][CH3:23])[C:17]([OH:19])=[O:18])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8857Ethyl AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 19969087HCID 19969087, compound

Product 1

HCID 540269032-(4-Octyloxyphenyl)-2-methoxyiminoacetic acidYield 55.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-octyloxyphenylglyoxylic acid (0.935 g) in a mixture of water (9 ml) and tetrahydrofuran (18 ml) and adjusted to pH 3.5-4 with 1N hydrochloric acid and methoxyamine hydrochloride (0.337 g) was added thereto at room temperature. The mixture was stirred for 2 hours at room temperature maintaining pH 3.5~4 with 1N hydrochloric acid. The reaction mixture was added to ethyl acetate. The organic layer was separated and dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure to give 2-(4-octyloxyphenyl)-2-methoxyiminoacetic acid (0.57 g).

Workup

  1. additionwas added
  2. customat room temperature
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe magnesium sulfate was filtered off
  6. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ec5ca92ca3be42ec8f465e1e2629fad3
Source dataset
uspto-grants-1994_12
Patent number
US05376634

Reaction notes

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