Toluene → 1,4-Benzenedicarboxylic acid, 1-methyl ester, potassium salt (1:1)

HRID 1089639Notes

Reaction equation

[O-]S([O-])(=O)=O.[Ca+2].[C:7]([O:19]C)(=[O:18])[C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=1.C1(C)C=CC=CC=1.[OH-].[K+:29]>CO>[C:12]([O:14][CH3:15])(=[O:13])[C:11]1[CH:16]=[CH:17][C:8]([C:7]([O-:19])=[O:18])=[CH:9][CH:10]=1.[K+:29]

Participants

Conditions

Temperature: 67.5 °C

Procedure

To a three-necked 50 ml round bottom flask equipped with a mechanical stirrer, reflux condenser and an addition funnel topped with a drying tube containing indicating Drierite® were added 2.70 gm (0.0139 mole) of dimethyl terephthalate (ex Aldrich Chemical Co.) and 15 ml of toluene. A solution containing 0.76 gm (0.0136 mole) of potassium hydroxide and 10 ml of methanol was added dropwise to the diester solution. The mixture formed an immediate emulsion. The emulsion was heated to 65-70° C. and soon thereafter a precipitate began to form. After 30 minutes the reaction was complete. The mixture was cooled to room temperature and the solid collected on a Buchner funnel. The filter cake was washed several times with warm toluene and ether; thereupon the cake was dried in a vacuum oven at 60° C. The yield was 2.85 gm (96%).

Workup

customTo a three-necked 50 ml round bottom flask equipped with a mechanical stirrer
temperaturereflux condenser and an addition funnel
customtopped with a drying tube
additioncontaining
customThe mixture formed an immediate emulsion
customto form
temperatureThe mixture was cooled to room temperature
customthe solid collected on a Buchner funnel
washThe filter cake was washed several times with warm toluene and ether
customthereupon the cake was dried in a vacuum oven at 60° C

Sources & evidence

ORD record: ord-8b901168809e47d8a144a20616cc9a20
Source dataset: uspto-grants-1992_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05078907

Reaction notes

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