Acetic Acid → Bis(4-hydroxyphenyl)methyloximinoacetic acid ethyl ester

HRID 861320Notes

Reaction equation

HRID 861320 reaction equation
[OH:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=O)=[CH:4][CH:3]=1.Cl.[NH2:18][O:19]CC(O)=O.[C:24]([OH:27])(=[O:26])[CH3:25].O1CCO[CH2:30][CH2:29]1.CCO.O>>[CH2:29]([O:26][C:24](=[O:27])[C:25]([CH:6]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:5]1[CH:15]=[CH:16][C:2]([OH:1])=[CH:3][CH:4]=1)=[N:18][OH:19])[CH3:30]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 691504,4'-DihydroxybenzophenoneHCID 101299582-(Aminooxy)acetic acid hydrochlorideHCID 69104347Dioxane ethanol water

Product 1

HCID 86752019Bis(4-hydroxyphenyl)methyloximinoacetic acid ethyl ester

Procedure

To a solution in dioxane/EtOH/H2O (3:2:1, 70 mL) of 4,4'-dihydroxy-benzophenone (3.21 g, 15 mmol) was added aminooxyacetic acid hydrochloride (3.25 g, 15 mmol) and acetic acid (0.5 mL). The mixture was refluxed for 18 hours, cooled to room temperature, and concentrated in vacuo. The residue was diluted with CH2Cl2 (100 mL), washed with saturated aqueous of NaHCO3 and brine, dried over MgSO4, filtered, and concentrated in vacuo. Chromatography on silica gel (hexanes/EtOAC 1: 1 ) provided bis(4-hydroxyphenyl)methyloximinoacetic acid ethyl ester (2.4 g).

Workup

  1. temperatureThe mixture was refluxed for 18 hours
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with CH2Cl2 (100 mL)
  4. washwashed with saturated aqueous of NaHCO3 and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-be372dc6b393444094cb816a839f69fd
Source dataset
uspto-grants-1998_02
Patent number
US05714488

Reaction notes

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