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

HRID 1922042Notes

Reaction equation

HRID 1922042 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.C([O-])([O-])=O.[K+].[K+].[OH:25][C:26]1[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[CH:28][CH:27]=1>C(O)(C)(C)C>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]([OH:17])[CH2:10][O:25][C:26]2[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[CH:28][CH:27]=2)=[N:7][CH:8]=1)[CH3:2]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 222462Pyridine, 5-ethyl-2-vinyl-2×

Product 1

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

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a flask fitted with an overhead stirrer, a thermometer and a condenser was added 500 g (3.759 mol) 5-ethyl-2-vinyl-pyridine dissolved in 7500 mL of 25% aqueous tertiary butanol. To this was added 802 g (4.5 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, 762 g (5.52 mol) of K2CO3 was added in one lot along with 537 g (4.4 mol) 4-hydroxy benzaldehyde. Reaction mixture was stirred for 18 hr. at 75-80° C. Subsequent work-up in water, extraction with ethyl acetate and purification yielded 805 g (79%) of the titled product. m.p. 83° C.

Workup

  1. customTo a flask fitted with an overhead stirrer
  2. customReaction mixture
  3. customThe progress of reaction
  4. customReaction mixture
  5. stirringwas stirred for 18 hr
  6. customat 75-80° C
  7. extractionSubsequent work-up in water, extraction
  8. customwith ethyl acetate and purification

Sources & evidence

ORD record
ord-4223a968cc5d424eb90f15776a5215c1
Source dataset
uspto-grants-2012_05
Patent number
US08173816B2

Reaction notes

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