Phthalic Acid → Diprop-2-en-1-yl 3,4,5,6-tetrachlorobenzene-1,2-dicarboxylate

HRID 1702504

Reaction equation

HRID 1702504 reaction equation
[C:1](OCC=C)(=O)[C:2]1C(=CC=C[CH:13]=1)C(OCC=C)=O.[CH2:19](Cl)[CH:20]=[CH2:21].C(O)(=O)C1C(=CC=CC=1)C(O)=O.[Cl:35][C:36]1[C:37]([Cl:50])=[C:38]([Cl:49])[C:39]([Cl:48])=[C:40]([C:45]([O-:47])=[O:46])[C:41]=1[C:42]([O-:44])=[O:43].[Na+].[Na+]>>[Cl:35][C:36]1[C:37]([Cl:50])=[C:38]([Cl:49])[C:39]([Cl:48])=[C:40]([C:45]([O:47][CH2:21][CH:20]=[CH2:19])=[O:46])[C:41]=1[C:42]([O:44][CH2:13][CH:2]=[CH2:1])=[O:43]

Participants

5

Reactant 4

HCID 1017Phthalic AcidHCID 7850Allyl chloride2×HCID 8560Diallyl phthalateHCID 20504075HCID 20504075, compound

Product 1

HCID 22450728Diprop-2-en-1-yl 3,4,5,6-tetrachlorobenzene-1,2-dicarboxylate

Procedure

Using a method similar to the known preparation of diallyl phthalate by reacting allyl chloride with metal salts of phthalic acid, Matsumoto et al prepared DATCP by reacting disodium tetrachlorophthalate with 2 moles of allyl chloride in an aqueous solution containing cuprous ions. Diallyl tetrachlorophthalate was also produced by Guseinov et al who reacted the anhydride with 3 moles of allyl alcohol plus 1 mole of hydrochloric acid in a benzene solution (Azerbaizhan Chemical Journal, No. 6, (1964), 21-23). Nordlander et al also produced DATCP by reacting the tetrachlorophthalic anhydride with 2 moles of allyl alcohol using sulfuric acid as a catalyst and driving off the water of reaction by distillation as an azeotrope with benzene (Journal of the American Chemical Society, 69, Nov., (1947), 2679-2682). However, only a 10% to 15% yield of the DATCP was obtained because of dehydration and polymerization reactions of the allyl alcohol.

Workup

  1. customprepared DATCP

Sources & evidence

ORD record
ord-9e0fc8d2fa924861befa2fd30dd70fbd
Source dataset
uspto-grants-1983_04
Patent number
US04381406

Linked notes

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