Oxalyl chloride → Monomethyl terephthalate chloride

HRID 37446

Reaction equation

HRID 37446 reaction equation
[C:1]([O:12][CH3:13])(=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6]([O-:8])=[O:7])=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:17])=O>CN(C=O)C.C1(C)C=CC=CC=1>[Cl-:17].[C:1]([O:12][CH3:13])(=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6]([O-:8])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 36144541,4-Benzenedicarboxylic acid, methyl ester

Product 1

HCID 22493623Monomethyl terephthalate chlorideYield 82%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
45 °C

Procedure

To a stirred solution of mono-methyl terephthalate (1 equivalent), toluene (30 ml/gm of ester) and 3 drops of DMF was added dropwise oxalyl chloride (2.0 equivalents). The reaction mixture was stirred at 45° C. for 16 hours. The solution was concentrated under reduced pressure to give the desired product as a pale yellow solid. The product was used without further purification; yield 82.0%; m.p. 50°-52° C. IR (thin film); 2970, 1775, 1720, 1430, 1400, 1280, 1105, 880 cm-1.

Workup

  1. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a280955a158d4e889882a189335a59c5
Source dataset
uspto-grants-1995_05
Patent number
US05420285

Linked notes

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