Dimethyl 2-[4-(hydroxymethyl)benzyl]-3-isopropylmaleate → 2-(4-Formylbenzyl)-3-isopropylmaleic acid dimethyl ester

HRID 1774404Notes

Reaction equation

HRID 1774404 reaction equation
[OH:1][CH2:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7]/[C:8](=[C:13](\[CH:18]([CH3:20])[CH3:19])/[C:14]([O:16][CH3:17])=[O:15])/[C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1>C1C=CC=CC=1.[O-2].[O-2].[Mn+4]>[CH3:12][O:11][C:9](=[O:10])/[C:8](/[CH2:7][C:6]1[CH:21]=[CH:22][C:3]([CH:2]=[O:1])=[CH:4][CH:5]=1)=[C:13](/[CH:18]([CH3:19])[CH3:20])\[C:14]([O:16][CH3:17])=[O:15]

Participants

4

Reactant 1

HCID 66648450Dimethyl 2-[4-(hydroxymethyl)benzyl]-3-isopropylmaleate

Product 1

HCID 866196432-(4-Formylbenzyl)-3-isopropylmaleic acid dimethyl esterYield 83.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 241BenzeneSolvent

Procedure

To a solution of dimethyl 2-[4-(hydroxymethyl)benzyl]-3-isopropylmaleate (96 mg, 0.31 mmol) in benzene (2.0 mL) was added active manganese dioxide (602 mg), and the mixture was vigorously stirred at room temperature for 3 h. After the reaction mixture was filtered, the filtrate was concentrated to dryness to give 79 mg of 2-(4-formylbenzyl)-3-isopropylmaleic acid dimethyl ester as colorless oil (yield: 83%).

Workup

  1. filtrationAfter the reaction mixture was filtered
  2. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-f4ba456a79674c76afd3e6c945e03cb9
Source dataset
uspto-grants-2016_02
Patent number
US09260375B2

Reaction notes

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