p-Toluenesulfonic acid → 1,3-Benzenedicarboxylic acid, 5-amino-, dibutyl ester
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:11]([OH:13])=[O:12])[CH:5]=[C:6]([C:8]([OH:10])=[O:9])[CH:7]=1.[C:14]1([CH3:24])[CH:19]=[CH:18]C(S(O)(=O)=O)=CC=1>C(O)CCC>[CH2:3]([O:12][C:11]([C:4]1[CH:3]=[C:2]([NH2:1])[CH:7]=[C:6]([C:8]([O:10][CH2:24][CH2:14][CH2:19][CH3:18])=[O:9])[CH:5]=1)=[O:13])[CH2:2][CH2:7][CH3:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 97 °C
Procedure
A mixture of 5-amino-1,3-benzenedicarboxylic acid (632 g, 3.49 mol), n-butyl alcohol (7.5 L) and p-toluenesulphonic acid (860 g, 4.52 mol) is loaded into a 10 L reaction vessel and heated to 97° C. under stirring under a reduced pressure of about 450 mBar removing the azeotrope n-butyl alcohol/water that forms. After 11 hours of heating the reaction mixture is concentrated to 2.4 L, cooled to 60° C. and neutralised by the addition of 5M NaOH (0.9 L). The mixture is further cooled to about 10° C. and diluted with water 3.4 L). After 15 hours at room temperature the solid is recovered by filtration, washed with water (2×1 L) and dried yielding the 5-amino-1,3-benzenedicarboxylic acid di-n-butyl ester (930 g, 3.17 mol, yield: 91%).
Workup
- customis loaded into a 10 L reaction vessel
- customremoving the azeotrope n-butyl alcohol/water that forms
- temperatureAfter 11 hours of heating the reaction mixture
- concentrationis concentrated to 2.4 L
- temperaturecooled to 60° C.
- additionneutralised by the addition of 5M NaOH (0.9 L)
- temperatureThe mixture is further cooled to about 10° C.
- additiondiluted with water 3.4 L)
- filtrationAfter 15 hours at room temperature the solid is recovered by filtration
- washwashed with water (2×1 L)
- customdried
Sources & evidence
- ORD record
- ord-5a7829f2a7764421a2e56a901fe4ecfc
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07244864B2
Reaction notes
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