Water → 2-(2,4,5-Trimethoxyphenyl)propanal

HRID 875296Notes

Reaction equation

HRID 875296 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([O:11][CH3:12])=[CH:5][C:4]=1[CH:13]=[CH:14]C.BrN1[C:21](=[O:22])CCC1=O.O>[Br-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.CS(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([O:11][CH3:12])=[CH:5][C:4]=1[CH:13]([CH3:14])[CH:21]=[O:22]

Participants

6

Reactant 3

HCID 962WaterHCID 179031,2,4-Trimethoxy-5-(1-propenyl)benzeneHCID 67184N-bromobutanimide

Product 1

HCID 468963042-(2,4,5-Trimethoxyphenyl)propanalYield 45%

Reagents, catalysts & solvents 2

HCID 5974Hexadecyltrimethylammonium BromideCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 2,4,5 trimethoxy phenyl propene (1 mmol), N-bromosuccinimide (1.5 mmol), water (12 ml), DMSO (3 ml), cetyltrimethyl ammonium bromide (0.3 mmol) was taken in a 100 ml Erlenmeyer flask fitted with loose funnel at the top. The flask was shaken well and placed inside the multimode microwave oven and irradiated (900 W) for 8 minutes in parts. After completion of reaction, the reaction mixture was worked up as in example-1 to provide the corresponding 2-(2,4,5 trimethoxy phenyl)propionaldehyde (45% yield) whose spectral data matched with that mentioned in example-1.

Workup

  1. customfitted with loose funnel at the top
  2. customirradiated (900 W) for 8 minutes in parts
  3. customAfter completion of reaction

Sources & evidence

ORD record
ord-9591cc3db5714cc1b1d527c9134aa818
Source dataset
uspto-grants-2015_03
Patent number
US08981152B2

Reaction notes

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