4-Hydroxybenzaldehyde → 4-[2-(5-Ethyl-2-pyridinyl)-2-hydroxyethoxy]benzaldehyde

HRID 1922046Notes

Reaction equation

HRID 1922046 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]=[CH2:10])=[N:7][CH:8]=1)[CH3:2].BrN1C(=[O:17])CCC1=O.[OH-].[Na+].[OH:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=[O:27])=[CH:24][CH:23]=1>O.C1(C)C=CC=CC=1.C(O)(C)(C)C>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]([OH:17])[CH2:10][O:21][C:22]2[CH:29]=[CH:28][C:25]([CH:26]=[O:27])=[CH:24][CH:23]=2)=[N:7][CH:8]=1)[CH3:2]

Participants

8

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 14798Sodium Hydroxide2×HCID 67184N-bromobutanimideHCID 222462Pyridine, 5-ethyl-2-vinyl-

Product 1

HCID 115507874-[2-(5-Ethyl-2-pyridinyl)-2-hydroxyethoxy]benzaldehydeYield 81%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent3×HCID 1140TolueneSolventHCID 6386tert-ButanolSolvent

Procedure

To a mixture of 690 mL tert-butanol and 2075 mL water, 184.46 g (1.3869 mol) of 5-ethyl-2-vinyl-pyridine was dissolved and under stirring 298.83 g (1.6788 mol) N-bromosuccinimide was added in 30 min. at 25-30° C. Stirring was continued for 1 hr. and 164.7 g (4.117 mol) of NaOH dissolved in 2075 mL water was added into it. Reaction mixture was stirred for 45 min. and extracted twice with 1000 mL methyl tert-butyl ether. Organic layers were combined, washed with brine, dried over magnesium sulfate and concentrated in vacuo to yield 190 g residual mass. The concentrated product obtained was added to a stirred mixture of 76 g (1.817 mol) NaOH dissolved in 1800 mL water and 223 g (1.817 mol) 4-hydroxy benzaldehyde dissolved in 1900 mL toluene. To this was added 16.65 g (0.063 mol) 18 Crown-6 and stirred for 24 hr. at 78° C. Subsequent work-up yielded 304.44 g (81%) 4-[2-(5-ethyl-pyridin-2-yl)-2-hydroxy-ethoxy]-benzaldehyde. m.p. 83° C.

Workup

  1. dissolutionwas dissolved
  2. additionwas added in 30 min. at 25-30° C
  3. additionwas added into it
  4. customReaction mixture
  5. stirringwas stirred for 45 min.
  6. extractionextracted twice with 1000 mL methyl tert-butyl ether
  7. washwashed with brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customto yield 190 g residual mass
  11. customThe concentrated product obtained
  12. stirringstirred for 24 hr
  13. customat 78° C

Sources & evidence

ORD record
ord-5011906e775444f4a823b893c504d414
Source dataset
uspto-grants-2012_05
Patent number
US08173816B2

Reaction notes

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