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

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

Reactant 4

HCID 176Acetic Acid

HCID 691504,4'-Dihydroxybenzophenone

HCID 101299582-(Aminooxy)acetic acid hydrochloride

HCID 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).