Reaction SMILES: [CH2:1](O)[CH2:2][CH2:3][CH3:4].[C:6]([OH:13])(=[O:12])[CH2:7][CH2:8][C:9]([OH:11])=[O:10]>>[C:6]([O:13][CH2:1][CH2:2][CH2:3][CH3:4])(=[O:12])[CH2:7][CH2:8][C:9]([O:11][CH2:1][CH2:2][CH2:3][CH3:4])=[O:10]
Reactant: O=C(O)CCC(=O)O
Reactant: CCCCO
Product: CCCCOC(=O)CCC(=O)OCCCC
Temperature: 80 °C
Reaction time: 1 h

Procedure:
A four-necked flask (equipped with a stirrer, a thermometer, a Dean-Stark apparatus, and a nitrogen gas inlet tube) was charged with 1700 g (22.9 mol) of 1-butanol (manufactured by Wako Pure Chemical Industries, Ltd.), 1042 g (8.82 mol) of succinic acid (manufactured by Wako Pure Chemical Industries, Ltd.), and 16.8 g (0.0882 mol) of paratoluenesulfonic acid monohydrate (manufactured by Wako Pure Chemical Industries, Ltd.), and the pressure was gradually dropped at 74° C. from 15.2 kPa to 6.9 kPa over 6.5 hours to distill off water. Thereafter, 28 g of KYOWAAD 500SH (manufactured by Kyowa Chemical Industry Co., Ltd.) was added thereto, and the mixture was stirred at a pressure of 4.0 kPa and 80° C. for 1 hour, and then filtered in vacuo. A four-neck flask (equipped with a stirrer, a thermometer, a distillation tube, and a nitrogen gas inlet tube) was charged with the filtrate, and the residual 1-butanol was distilled off by allowing the contents to react from a state of a pressure of 4.9 kPa and 75° C. to a state of a pressure of 2.7 kPa and 159° C. over 1 hour, and thereafter the residue was subjected to distillation at a pressure of 4.0 kPa while raising the temperature from 159° to 162° C., to provide dibutyl succinate. On the other hand, a four-necked flask (equipped with a stirrer, a thermometer, a distillation tube, and a nitrogen gas inlet tube) was charged with 461 g (4.34 mol) of diethylene glycol and 9.8 g of a methanol solution containing 28% by weight of sodium methoxide (sodium methoxide: 0.051 mol) as a catalyst, and methanol was distilled off, while stirring the contents at a pressure of 3.6 kPa and 84° C. for 0.5 hours. Thereafter, 3000 g (13.0 mol) of the dibutyl succinate mentioned above was added dropwise thereto over 3 hours at a pressure of 2.7 kPa and 90° C., and 1-butanol formed by the reaction was distilled off. Next, the temperature was raised to 130° C., and the pressure was gradually dropped from a normal pressure to 0.4 kPa over 1 hour to distill off 1-butanol. Thereafter, the pressure was recovered to a normal pressure, and further 2.5 g of a methanol solution containing 28% by weight sodium methoxide (sodium methoxide: 0.013 mol) was added as a catalyst. The pressure was gradually dropped at 130° C. from 2.7 kPa to 0.4 kPa over 1 hour to distill off 1-butanol. Thereafter, the residue was cooled to 80° C., 18 g of KYOWAAD 600S (manufactured by Kyowa Chemical Industry Co., Ltd.) was added thereto, and the mixture was stirred at a pressure of 4.0 kPa and 80° C. for 1 hour, and then filtered in vacuo. The filtrate was heated to a temperature of from 112° to 180° C. over 2 hours at a pressure of 0.3 kPa to distill off the residual dibutyl succinate, to provide a yellow liquid (ester compound J) at an ambient temperature. The amount of the catalyst used was 0.49 mol per 100 mol of the dicarboxylic acid ester.