Sodium Hydroxide → HCID 14068955, compound
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2([C:18]([O:20]CC)=[O:19])[CH2:12][CH:11]2[C:13]([O:15]CC)=[O:14])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[OH-].[Na+]>CO>[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2([C:18]([OH:20])=[O:19])[CH2:12][CH:11]2[C:13]([OH:15])=[O:14])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
14.2 g of diethyl 1-(3-nitrophenyl)-1,2-cyclopropanedicarboxylate are dissolved in 150 ml of methanol and to this solution are added 100 ml of 1N sodium hydroxide solution. The mixture is stirred overnight and the solvent is then removed from the dark brown solution. The reaction mixture is extracted twice with ether after cooling to 0° C. and adding 50 ml of 2N hydrochloric acid. The ethereal phases are washed repeatedly with a small amount of water, dried over magnesium sulfate, filtered and concentrated. The crystals so obtained are recrystallised from boiling ethyl acetate by adding petroleum ether. The title compound (d) is obtained in the form of pale beige-coloured crystals with m.p. 167°-170° C. and Rf=0.2 on thin-layer silica gel plates in the system methylene chloride/methanol/glacial acetic acid (40:5:1:).
Workup
- customthe solvent is then removed from the dark brown solution
- extractionThe reaction mixture is extracted twice with ether
- additionadding 50 ml of 2N hydrochloric acid
- washThe ethereal phases are washed repeatedly with a small amount of water
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe crystals so obtained
- customare recrystallised
- additionby adding petroleum ether
Sources & evidence
- ORD record
- ord-3cc53d68b95a41819b250499aa4ccdfd
- Source dataset
- uspto-grants-1989_06
- Patent number
- US04839379
Reaction notes
Loading…