Dimethylformamide → (2E)-2-Benzylidenebutanedioic Acid

HRID 988312Notes

Reaction equation

HRID 988312 reaction equation
C([C:5]1[CH:15]=[CH:14][C:8](/[CH:9]=[CH:10]/[C:11]([OH:13])=[O:12])=[CH:7][CH:6]=1)(OC)=O.[C:16](Cl)(=[O:20])[C:17](Cl)=O.CN(C=[O:26])C>C1COCC1>[C:16]([CH2:17]/[C:10](=[CH:9]\[C:8]1[CH:7]=[CH:6][CH:5]=[CH:15][CH:14]=1)/[C:11]([OH:13])=[O:12])([OH:20])=[O:26]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 1472795(2E)-3-(4-(methoxycarbonyl)phenyl)prop-2-enoic acid

Product 1

HCID 820629(2E)-2-Benzylidenebutanedioic Acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of (E)-4-carbomethoxycinnamic acid (5.09 g, 24.7 mmol) was dissolved in dry THF (25 mL) and treated under an argon atmosphere with oxalyl chloride (3.00 mL, 34.4 mmol) and a drop of dry DMF. After heating at 50° C. for 2 hours, the reaction mixture was concentrated in vacuo to yield the acid chloride of (E)-carboxymethyl cinnamic acid as a tan solid.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-19270234b4cd4df8bfc669c1a8b43926
Source dataset
uspto-grants-2003_10
Patent number
US06635638B2

Reaction notes

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