Syringaldehyde → 105482-74-4

HRID 1603739Notes

Reaction equation

HRID 1603739 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:12][CH3:13])[C:10]=1[OH:11])[CH:6]=O.[F:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:12][CH3:13])[C:10]=1[OH:11])[CH:6]=[N:19][C:18]1[CH:20]=[CH:21][C:15]([F:14])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 8655SyringaldehydeHCID 97314-Fluoroaniline

Product 1

HCID 135752758105482-74-4

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3,5-Dimethoxy-4-hydroxybenzaldehyde (1 g, 5.46 mmol) was dissolved in methanol (30 ml) and to this solution was added 4-fluoroaniline (600 mg, 5.46 mmol, 0.51 ml). The resultant reaction solution was stirred for forty-eight (48) hours at room temperature under nitrogen. The reaction solution was then cooled in the freezer and the resultant precipitate was isolated by filtration and washed with cold methanol and ether. The isolated light yellow powder was the title product: 1H NMR (300 MHz, CDCl3); δ 8.31 (S, 1H), 7.20-7.04 (m, 4H) 5.85 (S, 1H), 3.98 (S, 6H).

Workup

  1. customThe resultant reaction solution
  2. temperatureThe reaction solution was then cooled in the freezer

Sources & evidence

ORD record
ord-b4eed5b8f9cb4e698142bfbecf5c3325
Source dataset
uspto-grants-1999_11
Patent number
US05990137

Reaction notes

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