Tetrachlorophthalic anhydride → 2,3,4,5-Tetrachlorobenzoic acid

HRID 1449095Notes

Reaction equation

[Cl:1][C:2]1[C:3]([Cl:15])=[C:4]([Cl:14])[C:5]([Cl:13])=[C:6]2[C:11](=[O:12])[O:10]C(=O)[C:7]=12.C(N1C2C(=CC=CC=2)C=C1C)CCCCCCC.[Cl-].[Al+3].[Cl-].[Cl-]>>[Cl:1][C:2]1[CH:7]=[C:6]([C:5]([Cl:13])=[C:4]([Cl:14])[C:3]=1[Cl:15])[C:11]([OH:12])=[O:10]

Participants

Reactant 3

HCID 8326Tetrachlorophthalic anhydride

HCID 1707081H-Indole, 2-methyl-1-octyl-

HCID 6451240Aluminum(III) Chloride

Product 1

HCID 57822,3,4,5-Tetrachlorobenzoic acid

Procedure

Proceeding in the same manner as that described in part A of Example 6 above, 14.3 g (0.05 mole) of tetrachlorophthalic anhydride, 16.0 g (0.052 mole) of 76.5 percent active 1-n-octyl-2-methylindole and 13.3 g (0.10 mole) of aluminum chloride were interacted to obtain 2-[(1-n-octyl-2-methyl-3-indolyl)carbonyl[-3,4,5,6-tetrachlorobenzoic acid (Formula VIII: R°=R1 =R2 =R3 =Cl; R5 =CH3 ; R6 =(CH2)7CH3 ; Y1 =H), a pale orange solid melting at 132°-134° C. The infrared spectrum, showing a maximum at 1745 cm-1 (C=O; s) and the nuclear magnetic resonance spectrum was in accord with the structure.

Sources & evidence

ORD record: ord-c34c25c142684fce9da115ab688273bb
Source dataset: uspto-grants-1980_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04189171

Reaction notes

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