P-Anisidine → HCID 135752759, compound

HRID 1585733Notes

Reaction equation

HRID 1585733 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])[CH:8]=O)([CH3:4])([CH3:3])[CH3:2].[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=1>CO>[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])[CH:8]=[N:26][C:23]1[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[CH:21][CH:22]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehyde

Product 1

HCID 135752759HCID 135752759, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3,5-di(Tert-butyl)-4-hydroxybenzaldehyde (1 g, 4.11 mmol) was dissolved in methanol (30 ml). To this solution was added p-anisidine (0.51 g, 4.11 mmol). The resultant reaction solution was stirred at room temperature under nitrogen for two (2) hours and the solution was taken to dryness in vacuo. The resultant oil was azeotroped with methanol (2x), ether (1x), a mixture of ethyl acetate/hexane (1x), and methanol (1x). The oil was left in vacuo overnight which began crystallization of the oil. The crystals were then dissolved in a mixture of ether and hexane. Dark flakes of p-anisidine were filtered out of the solution, the mother liquor was reduced with low heat, resulting in crystals of the title product which were collected by filtration: 1H NMR (300 MHz, CDCl3) ; δ 8.38 (S, 1H) , 7.72 (S, 2H), 7.19 (d, J=9 Hz, 1H), 6.90 (d, J=9 Hz, 2H), 5.58 (S, 1H), 3.83 (S, 3H).

Workup

  1. customThe resultant reaction solution
  2. customThe resultant oil was azeotroped with methanol (2x), ether (1x)
  3. additiona mixture of ethyl acetate/hexane (1x), and methanol (1x)
  4. customcrystallization of the oil
  5. dissolutionThe crystals were then dissolved in a mixture of ether and hexane
  6. filtrationDark flakes of p-anisidine were filtered out of the solution

Sources & evidence

ORD record
ord-fbeb2d5db41245709a80d8b714208114
Source dataset
uspto-grants-1999_08
Patent number
US05939460

Reaction notes

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