Vanillin → 24033-07-6

HRID 1585734Notes

Reaction equation

HRID 1585734 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[OH:11])[CH:6]=O.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1.CCOCC.C(OCC)(=O)C.CCCCCC>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[OH:11])[CH:6]=[N:20][C:17]1[CH:18]=[CH:19][C:14]([O:13][CH3:12])=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 1183VanillinHCID 3283Diethyl Ether2×HCID 7732P-AnisidineHCID 21226206Ethyl acetate hexane

Product 1

HCID 68137024033-07-6

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Methoxy-4-hydroxybenzaldehyde (vanillin, 1 g, 6.57 mmol) was dissolved in methanol (30 ml). To this solution was added p-anisidine (0.810 g, 6.57 mmol) and the resultant reaction solution was stirred overnight under nitrogen at room temperature. The reaction solution was taken to dryness in vacuo with the application of heat. The resultant solid was azeotropically mixed with methanol (2x), ether (1x), and again with methanol (2x) to yield yellow crystals. The crystals were triturated with hot ether to yield the title product: 1H NMR (300 MHz, CDCl3); δ 8.36 (S, 1H), 7.60 (S, 1H), 7.30-7.17 (m, 3H), 7.05-6,91 (m, 3H), 6.10 (S, 1H), 3.97 (S, 3H), 3.83 (S, 3H).

Workup

  1. customthe resultant reaction solution
  2. temperatureof heat
  3. customThe crystals were triturated with hot ether

Sources & evidence

ORD record
ord-1e2f7b934bc244598df4f763b1bffd6b
Source dataset
uspto-grants-1999_08
Patent number
US05939460

Reaction notes

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