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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1834409Generated: October 27, 2026

Formaldehyde → 2,3,4,5-Tetramethylpyrrole

https://huagongshe.com/reaction/1834409

Reaction equation

Participants

RoleNameHCIDCharge
ReactantFormaldehydeHCID 712—
ReactantHydrogen iodideHCID 24841—
Reactant1H-Pyrrole-2-carboxylic acid, 3,5-dimethyl-, ethyl esterHCID 137477—
ReactantEthyl 3,4,5-trimethyl-1H-pyrrole-2-carboxylateHCID 137479—
SolventAcetic AcidHCID 176—
SolventDiethyl EtherHCID 3283—
Product2,3,4,5-TetramethylpyrroleHCID 70484—

Reaction Steps

2,4-Dimethyl-5-carbethoxy-pyrrole (1.64 g), acetic acid (25 ml), aqueous hydriodic acid (25 ml) and paraformaldehyde (0.589g), were heated at 95°-100° C. for three hours under nitrogen with stirring. The work up was the same as that of 2,3,4-trimethyl-5-carbethoxy-pyrrole in Example 4 except the 2 × 75 ml of ether was used and care was taken to avoid exposure of the product to air. It was purified by distillation (10 mm, 60° C.) to give 0.628 g (52%), m.p. 106°-108° C. (lit4 m.p. 111°-112° C.).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04070366
Source datasetuspto-grants-1978_01
ORD IDord-5c8adf5c0bd942a6807bf945faa80846
Source noteuspto-grants-1978_01