2,4,5-Trimethoxybenzaldehyde → HCID 53767826, compound

HRID 1900088Notes

Reaction equation

HRID 1900088 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[CH:7][C:4]=1[CH:5]=O.[Br:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]#[N:24])=[CH:18][CH:17]=1>C(O)C.[OH-].[Na+]>[C:23]([C:22](=[CH:5][C:4]1[CH:7]=[C:8]([O:13][CH3:14])[C:9]([O:11][CH3:12])=[CH:10][C:3]=1[O:2][CH3:1])[C:19]1[CH:20]=[CH:21][C:16]([Br:15])=[CH:17][CH:18]=1)#[N:24]

Participants

5

Reactant 2

HCID 205252,4,5-TrimethoxybenzaldehydeHCID 27914Benzeneacetonitrile, 4-bromo-

Product 1

HCID 53767826HCID 53767826, compoundYield 95.7%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalystHCID 702EthanolSolvent2×

Procedure

A mixture of 1.96 g (10.0 mmol) of 2,4,5-trimethoxybenzaldehyde (purchased from Lancaster), and 1.96 g (10.0 mmol) of 4-bromophenylacetonitrile (purchased from Tokyo Kasei) in 5 ml of ethanol (purchased from Kokusan Kagaku) was heated to dissolve. Two drops of 20% aqueous sodium hydroxide solution was then added and the reaction mixture was stirred over night at ambient temperature. To the resultant reaction mass was added ethanol and crushed, and the precipitate was collected and washed with ethanol twice and with hexane twice, and dried to give 3.58 g (yield: 95.6%) of α-cyano-4-bromo-2',4',5'-trimethoxystilbene (as a yellow crystalline).

Workup

  1. temperaturewas heated to dissolve
  2. customTo the resultant reaction mass
  3. customcrushed
  4. customthe precipitate was collected
  5. washwashed with ethanol twice
  6. dry with materialwith hexane twice, and dried

Sources & evidence

ORD record
ord-f1b7f8e88ef34803a14f33835eca83dd
Source dataset
uspto-grants-1996_11
Patent number
US05574062

Reaction notes

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