Dimethylamine → 2-(2-Methylpropoxy)benzoic acid
Reaction equation
CNC.Cl[C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]>C(O)C(C)C>[CH2:7]([O:8][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])[CH:6]([CH3:10])[CH3:5]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
In a pressure-resistant sealed vessel, were dissolved 1.14 g of o-chlorobenzoic acid (7.3 mM) and 0.18 g of cuprous chloride (1.8 mM) in 5 g of an isobutyl alcohol solution containing 20% dimethylamine (about 6.0 ml) prior to addition of isobutyl alcohol to a total volume of 50 ml, followed by heating to 100° C. as in Example 4. The reaction mixture solution was analyzed periodically over time by GC-MSE1 in the same manner as in Example 4, in order to follow the progress of the reaction. As a result, 20 hours later, the completion of the reaction was confirmed. Effecting the subsequent process in the same manner as in Example 4, 1.0 g of 2-isobutoxybenzoic acid was obtained (yield of 70.6%). The ester of the above product (3%) and benzoic acid (5%) were also obtained as the byproducts, which were confirmed by 1H-NMR and GC-MSE1.
Workup
- customthe progress of the reaction
- customAs a result, 20 hours
Sources & evidence
- ORD record
- ord-9f3e5786e1ed4b6ba3f622ea336392d3
- Source dataset
- uspto-grants-1994_09
- Patent number
- US05344968
Reaction notes
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