Sulfuric Acid → Ethyl 11-bromoundecanoate
Reaction equation
N[C:2]1C(I)=C(CCCCCCCCCCCC(O)=O)C(I)=C[C:7]=1I.[Br:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([OH:38])=[O:37].OS(O)(=O)=O>C(O)C>[CH2:2]([O:37][C:36](=[O:38])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][Br:25])[CH3:7]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
In this example, 12-(3-amino-2,4,6-triiodophenyl)-dodecanoic acid is synthesized. 11-Bromoundecanoic acid (54.0 g, 200 mmol) was refluxed overnight with 150 ml absolute ethanol and a catalytic amount (1.0 ml) H2SO4. The solvent was removed in vacuo and the residue was dissolved in 100 ml CHCl3 and extracted with 100 ml H2O, twice with 100 ml 10% aq. NaHCO3, 100 ml water, and brine, and was dried with MgSO4. Removal of the solvent in vacuo and distillation of the remaining yellow liquid under vacuum yielded ethyl-11-bromoundecanoate as a colorless liquid.
Workup
- customThe solvent was removed in vacuo
- dissolutionthe residue was dissolved in 100 ml CHCl3
- extractionextracted with 100 ml H2O, twice with 100 ml 10% aq. NaHCO3, 100 ml water, and brine
- dry with materialwas dried with MgSO4
- customRemoval of the solvent
- distillationin vacuo and distillation of the remaining yellow liquid under vacuum
Sources & evidence
- ORD record
- ord-7dc3c6944a2442b8949551b9384a1996
- Source dataset
- uspto-grants-1992_03
- Patent number
- US05093042
Reaction notes
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