Hydrochloric Acid → methyl 5-[(E)-2-carboxyethenyl]-3-iodobenzoate

HRID 1740307Notes

Reaction equation

HRID 1740307 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([I:13])[CH:6]=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])=O.C(O)(=O)[CH2:15][C:16]([OH:18])=[O:17].N1CCCCC1.Cl>N1C=CC=CC=1.O>[C:16](/[CH:15]=[CH:1]/[C:3]1[CH:4]=[C:5]([I:13])[CH:6]=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])([OH:18])=[O:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 21838328Methyl 3-formyl-5-iodobenzoate

Product 1

HCID 21838304methyl 5-[(E)-2-carboxyethenyl]-3-iodobenzoateYield 83.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

The mixture of methyl 5-formyl-3-iodobenzoate (2.5 g), malonic acid (1.8 g) and piperidine (0.2 ml) in pyridine (25 ml) was stirred for 3 hours at 100° C. The mixture was added to water and adjusted to pH 2 with 6N-hydrochloric acid. The isolated precipitate was collected by filtration to give methyl 5-[(E)-2-carboxyethenyl]-3-iodobenzoate (2.4 g)

Workup

  1. filtrationThe isolated precipitate was collected by filtration

Sources & evidence

ORD record
ord-b0477cdb665e44c5bcb83e40fb36b959
Source dataset
uspto-grants-1999_10
Patent number
US05968985

Reaction notes

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