2-Nitrophenol → 2,2'-Oxybis(nitrobenzene)
Reaction equation
[OH-:1].[K+].[N+:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12])([O-:5])=[O:4]>>[N+:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[N+:3]([O-:4])=[O:1])([O-:5])=[O:4]Participants
3
Procedure
From N-Boc-D-cHyp(Tosyloxy)-OMe (5.27 mmol, 2.50 g), powdered KOH (13.2 mmol, 0.74 g), and 2-nitrophenol (13.2 mmol, 1.83 g), held at reflux for 6 days, the 2-nitrophenyl ether of D-trans-hydroxyproline methyl ester (0.29 g, 14%) was obtained. Purification by column chromatography (silica ge, ethyl acetate/hexane mixtures) yielded no pure fractions. All fractions bearing product were combined and purified in three equal portions using the chromatotron (4 mm silica gel plates) and a mixture of ethyl acetate/CH2Cl2/hexane (2:9:9:) which was found to effect separation on TLC plates. The mixture of ethyl acetate/CH2Cl2 (2:9) will be referred to as mixture A or simply A.
Workup
- temperatureat reflux for 6 days
Sources & evidence
- ORD record
- ord-b500d7de56234a4aae507e1e396f8edc
- Source dataset
- uspto-grants-2001_09
- Patent number
- US06288036B1
Reaction notes
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