Sulfuric Acid → 3-Iodo-4-cyclohexylphenylglyoxylic acid

HRID 261579

Reaction equation

N[C:2]1[CH:3]=[C:4]([C:14](=[O:20])[C:15]([O:17]CC)=[O:16])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.S(=O)(=O)(O)O.N([O-])=O.[Na+].[I-:30].[K+]>[Cu].O>[I:30][C:2]1[CH:3]=[C:4]([C:14](=[O:20])[C:15]([OH:17])=[O:16])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

Conditions

Temperature: 80 °C

Procedure

To 0.05 moles of ethyl 3-amino-4-cyclohexylphenylglyoxylate dissolved in a mixture of 50 g. of ice water and 0.06 moles of concentrated sulfuric acid at 0° C. is added a solution of 0.05 moles of 95% sodium nitrite in 8 ml. of water. Stirring is continued for 1/2 hour and then 1.5 ml. of concentrated sulfuric acid is added. This solution is poured into an ice cold solution of 0.06 moles of potassium iodide in 10 ml. of water. To this is added 0.075 g. copper bronze with stirring and the solution is warmed slowly on a water bath to about 80° C. for 2 hours. After cooling to room temperature the reaction mixture is extracted thrice with 15 ml. portions of chloroform. This is then washed with dilute thiosulfate solution, water, dried over sodium sulfate and evaporated in vacuo. The residue is crystallized to obtain 3-iodo-4-cyclohexylphenylglyoxylic acid.

Workup

additionTo this is added 0.075 g
temperatureAfter cooling to room temperature the reaction mixture
extractionis extracted thrice with 15 ml
washThis is then washed with dilute thiosulfate solution, water
dry with materialdried over sodium sulfate
customevaporated in vacuo
customThe residue is crystallized

Sources & evidence

ORD record: ord-a619d0e13c9a4b629f24938ae398d979
Source dataset: uspto-grants-1979_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04166133

Linked notes

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