Benzene → 3-Hydroxy-5-keto-4-phenylazo-3-cyclohexane-carboxylic acid methyl ester
Reaction equation
[OH:1][C:2]1[CH2:3][CH:4](C(O)=O)[CH2:5][C:6](=[O:16])[C:7]=1[N:8]=[N:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH3:20][OH:21].[CH:22]1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH2:39]>>[CH3:20][O:21][C:22]([C:2]1([OH:1])[CH:7]([N:8]=[N:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:6](=[O:16])[CH2:5][CH2:4][CH2:3]1)=[O:39]Participants
6
Procedure
60 G. of 3-hydroxy-5-keto-4-phenylazo-3-cyclohexene-carboxylic acid, 200 ml. of methanol, 1200 ml. of benzene and 5 g. of p-toluenesulfonic acid were boiled together under reflux on a water separator for 18 hours. After cooling, the solution was washed with 500 ml. of a 5% sodium bicarbonate solution, then washed with water, dried and evaporated. The residue was dissolved in ethyl acetate and purified on an aluminum oxide column (500 g.; activity stage I). After evaporation of the ethylacetate, there was obtained 3-hydroxy-5-keto-4-phenylazo-3-cyclohexane-carboxylic acid methyl ester as a solid having a melting point of 144° C.
Workup
- temperatureAfter cooling
- washthe solution was washed with 500 ml
- washof a 5% sodium bicarbonate solution, then washed with water
- customdried
- customevaporated
- dissolutionThe residue was dissolved in ethyl acetate
- custompurified on an aluminum oxide column (500 g.; activity stage I)
- customAfter evaporation of the ethylacetate
Sources & evidence
- ORD record
- ord-868bf62f9f3b4577a5c68b4a81b9ce0b
- Source dataset
- uspto-grants-1985_05
- Patent number
- US04515948
Reaction notes
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