Water → 2-(4-Carboxybenzyl)-3-isopropylmaleic acid dimethyl ester

HRID 1774405Notes

Reaction equation

HRID 1774405 reaction equation
[CH3:1][O:2][C:3](=[O:22])/[C:4](/[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]=[O:21])=[CH:16][CH:15]=1)=[C:5](/[CH:10]([CH3:12])[CH3:11])\[C:6]([O:8][CH3:9])=[O:7].[O:23]1CCOCC1.O.Cl([O-])=O.[Na+]>CCCCCC.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:22])/[C:4](/[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([OH:23])=[O:21])=[CH:16][CH:15]=1)=[C:5](/[CH:10]([CH3:11])[CH3:12])\[C:6]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 312751,4-DioxaneHCID 23668197Sodium ChloriteHCID 866196432-(4-Formylbenzyl)-3-isopropylmaleic acid dimethyl ester

Product 1

HCID 666486782-(4-Carboxybenzyl)-3-isopropylmaleic acid dimethyl esterYield 96%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a suspension of 2-(4-formylbenzyl)-3-isopropylmaleic acid dimethyl ester (79 mg, 0.259 mmol) in a mixed solvent of dioxane (3.0 mL) and water (3.0 mL) were added amide sulfate (38 mg, 0.39 mmol) and sodium chlorite (35 mg, 0.39 mmol) with stirring under ice cooling, and the mixture was stirred for 30 min. The reaction mixture was directly concentrated, and the residue thus obtained was subjected to silica gel column chromatography (hexane-ethyl acetate 1:2) to give 80 mg of the title compound as oil (yield: 96%).

Workup

  1. stirringthe mixture was stirred for 30 min
  2. concentrationThe reaction mixture was directly concentrated
  3. customthe residue thus obtained

Sources & evidence

ORD record
ord-087f7d76969845e8b257961d00fea571
Source dataset
uspto-grants-2016_02
Patent number
US09260375B2

Reaction notes

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