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

HRID 882103Notes

Reaction equation

HRID 882103 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.[K].[OH:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=1>C(O)(C)(C)C>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]([OH:17])[CH2:10][O:20][C:21]2[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=2)=[N:7][CH:8]=1)[CH3:2]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 67184N-bromobutanimideHCID 222462Pyridine, 5-ethyl-2-vinyl-2×HCID 5462222Potassium

Product 1

HCID 115507874-[2-(5-Ethyl-2-pyridinyl)-2-hydroxyethoxy]benzaldehydeYield 79%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of 5 g (0.03759 mol) 5-ethyl-2-vinyl-pyridine dissolved in 75 mL of 25% aqueous tertiary butanol added 8.02 g (0.045 mol) N-bromosuccinimide at 25-30° C. in 30 min. Reaction mixture was stirred for 2 hr. The progress of reaction was monitored by TLC and after complete consumption of the 5-ethyl-2-vinyl-pyridine, 6.01 g (0.03759 mol) potassium salt of 4-hydroxy benzaldehyde was added. Reaction mixture was stirred for 18 hr. at 75-80° C. Subsequent work-up in water and extraction with ethyl acetate yielded 8.04 g (79%) of the titled product. m.p. 81° C.

Workup

  1. customReaction mixture
  2. customThe progress of reaction
  3. additionwas added
  4. customReaction mixture
  5. stirringwas stirred for 18 hr
  6. customat 75-80° C
  7. extractionSubsequent work-up in water and extraction with ethyl acetate

Sources & evidence

ORD record
ord-8a4f0cf841d9438a9c52056e1f11fd9c
Source dataset
uspto-grants-2015_03
Patent number
US08993773B2

Reaction notes

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