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Dichloromethane → Terephthaloyl chloride

HRID 65889
Notes
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Reaction equation

HRID 65889 reaction equation
[C:1]([OH:12])(=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.[Cl:13][CH2:14]Cl.[C:16]([Cl:19])(Cl)=[O:17]>N1C=CC=CC=1>[C:6]([O:17][CH3:16])(=[O:8])[C:5]1[CH:4]=[CH:3][C:2]([C:1]([O:12][CH3:14])=[O:11])=[CH:10][CH:9]=1.[C:16]([Cl:19])(=[O:17])[C:5]1[CH:9]=[CH:10][C:2]([C:1]([Cl:13])=[O:12])=[CH:3][CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6344Dichloromethane2×HCID 6371PhosgeneHCID 7489Terephthalic Acid

Product 2

HCID 7488Terephthaloyl chlorideYield 94.2%HCID 8441Dimethyl terephthalate

Reagents, catalysts & solvents 1

HCID 1049Pyridine
Solvent
2×

Procedure

Following the general procedure of Example 9, a slurry of 7.13 parts terephthalic acid in 80 parts dry dichloromethane was added to a mixture of 6.93 parts pyridine and 9.35 parts phosgene in 210 parts dry dichloromethane at 25° to 30° C. The ratio of equivalents of pyridine base/COOH acid group was 1.02. After carrying out the reaction and esterifying the resulting diacid chloride by the procedure as described in Example 1, there was obtained a 94.2% yield of theory of dimethyl terephthalate corresponding to a 94.2% yield of terephthaloyl chloride formed initially in the reaction.

Workup

  1. customthe reaction

Sources & evidence

ORD record
ord-7b95d68545324b8d9bd6d2665bf5600b
Source dataset
uspto-grants-1978_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04129594

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes