Piperonyl alcohol → HCID 69693236, compound

HRID 583757Notes

Reaction equation

C(N1[CH:12]=[CH:11]N=C1)(N1C=CN=C1)=O.[S:13]1[CH:17]=[C:16]([C:18]([OH:20])=[O:19])[CH:15]=[C:14]1[C:21]([OH:23])=[O:22].[CH2:24](O)[C:25]1[CH:33]=[CH:32][C:31]2[O:30][CH2:29][O:28][C:27]=2[CH:26]=1>>[O:30]1[C:31]2[CH:32]=[CH:33][C:25]([CH:24]([O:22][C:21]([C:14]3[S:13][CH:17]=[C:16]([C:18]([OH:20])=[O:19])[CH:15]=3)=[O:23])[C:12]3[CH:11]=[CH:26][C:27]4[O:28][CH2:29][O:30][C:31]=4[CH:32]=3)=[CH:26][C:27]=2[O:28][CH2:29]1

Participants

Reactant 3

HCID 10322Piperonyl alcohol

HCID 682631,1'-Carbonyldiimidazole

HCID 255851Thiophene-2,4-dicarboxylic acid

Product 1

HCID 69693236HCID 69693236, compoundYield 114.8%

Procedure

The title compound was prepared according to the procedure described for Example 2 using carbonyldiimidazole (1.1 g, 6.8 mmol), 2,4-thiophene-dicarboxylic acid (0.5 g, 2.9 mmol) and piperonyl alcohol (0.45 g, 2.9 mmol). Acidification of the aqueous workup mixture with dilute hydrochloric acid prior to filtration afforded 0.71 g of thiophene-2,4-dicarboxylic acid di-1,3-benzodioxol-5-ylmethyl ester. Recrystallization of a sample from methanol followed by trituration in ethyl acetate then ether and drying gave product with a mp 164-165° C.

Workup

customThe title compound was prepared
filtrationAcidification of the aqueous workup mixture with dilute hydrochloric acid prior to filtration

Sources & evidence

ORD record: ord-1b9be2b1d26c426d8d139978aa64840f
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06924276B2

Reaction notes

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