Oxalyl chloride → 3-(4-Nitrophenyl)propionyl chloride
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]([OH:14])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(Cl)(=O)C([Cl:18])=O>C(Cl)Cl.CN(C=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]([Cl:18])=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
3-(4-Nitrophenyl)propanoic acid prepared in Example DD (12.5 g, 64 mmol) was suspended in CH2Cl2 (300 mL) and treated with oxalyl chloride (7.4 mL, 85 mmol) and DMF (5 drops). The solution was stirred overnight at room temperature. The solution was concentrated, and the residue was dissolved in CH2Cl2 and re-concentrated. The crude product was used as is in the next step.
Workup
- concentrationThe solution was concentrated
- dissolutionthe residue was dissolved in CH2Cl2
- concentrationre-concentrated
Sources & evidence
- ORD record
- ord-9d995b24aa6f4bc1bc16cc3926527678
- Source dataset
- uspto-grants-1998_11
- Patent number
- US05834506
Reaction notes
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