1,2,4-Trimethoxy-5-(1-propenyl)benzene → 2-(2,4,5-Trimethoxyphenyl)propanal

HRID 875297Notes

Reaction equation

HRID 875297 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>[Br-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.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

5

Reactant 2

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

Product 1

HCID 468963042-(2,4,5-Trimethoxyphenyl)propanalYield 43%

Reagents, catalysts & solvents 2

HCID 5974Hexadecyltrimethylammonium BromideCatalystHCID 962WaterSolvent

Procedure

A mixture of 2,4,5 trimethoxy phenyl propene (1 mmol), N-bromosuccinimide (1.2 mmol), water (14 ml), cetyltrimethyl ammonium bromide (0.3 mmol) were taken in a 100 ml round bottom flask fitted with a condenser. The flask was shaken well and placed inside the monomode microwave oven and irradiated (220 W, 200° C.) for 12 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 (43% yield) whose spectral data matched with that mentioned in example-1.

Workup

  1. customwere taken in a 100 ml round bottom flask
  2. customfitted with a condenser
  3. customirradiated (220 W, 200° C.) for 12 minutes in parts
  4. customAfter completion of reaction

Sources & evidence

ORD record
ord-1cf94b7e89a94887bb3a365141137935
Source dataset
uspto-grants-2015_03
Patent number
US08981152B2

Reaction notes

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