Oxalyl chloride → HCID 59627906, compound
Reaction equation
[CH3:1][C:2](=[CH2:10])[CH2:3][CH2:4][CH2:5][CH2:6][C:7](O)=[O:8].C(Cl)(=O)C([Cl:14])=O>C1C=CC=CC=1>[CH3:1][C:2](=[CH2:10])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([Cl:14])=[O:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of the carboxylic acid 71 (2.2 g, 15.5 mmol) in benzene (30 ml), was added oxalyl chloride (3 ml, 34.4 mmol, 2.22 equiv). A drying tube was placed on the flask and the reaction mixture was stirred for 90 min at room temperature before it was concentrated in vacuo. The crude acid chloride was used in the next step without further purification: TLC Rf=0.37 (silica gel, 25% EtOAc/hexanes); 1H NMR (600 MHz, CDCl3) δ 4.69 (s, 1H), 4.67 (s, 1H), 2.90-2.87 (t, 3J=7.8 Hz, 2H), 2.03-2.00 (t, 3J=7.8 Hz, 2H), 1.74-1.66 (m, 2H), 1.69 (s, 3H), 1.58-1.46 (m, 2H); 13C NMR (100 MHz, CDCl3) δ 173.979, 145.086, 110.717, 46.663, 37.334, 26.421, 24.799, 22.431.