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

HRID 1922043Notes

Reaction equation

HRID 1922043 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>C(O)(C)(C)C.O.C1(C)C=CC=CC=1>[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 84%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 6386tert-ButanolSolvent

Procedure

To a flask fitted with an overhead stirrer, a thermometer and a condenser was added a solution of 12 Kg (90.22 mole) 5-ethyl-2-vinyl-pyridine dissolved in a mixture of 45 lit. tert-butanol and 135 lit. water at 25° C., followed by addition of 19.26 Kg (108.25 mole) N-bromosuccinimide and reaction mixture was stirred for 1.5 hr. 135 lit. aqueous 2N NaOH solution was added to the reaction mixture and stirring was continued for further 45 min. Progress of reaction was monitored by TLC and after completion of reaction, product was extracted with 120 lit. methylene chloride. Layers were separated, organic layer was washed with 72 lit. brine solution, dried (magnesium sulfate) and concentrated under reduced pressure. The residual mass obtained was added into a stirred mixture of 15.96 Kg (130.8 mole) 4-hydroxy benzaldehyde dissolved in 130 lit. toluene and 5.23 Kg (1307 mole) NaOH dissolved in 120 lit. water. To this was added 2.21 Kg PEG 4000 and stirred for 17 hr. at 78° C. Subsequent work-up gave 20.538 Kg (84%) 4-[2-(5-ethyl-pyridin-2-yl)-2-hydroxy-ethoxy]-benzaldehyde. m.p. 82° C.

Workup

  1. customTo a flask fitted with an overhead stirrer
  2. stirringstirring
  3. waitwas continued for further 45 min
  4. customProgress of reaction
  5. customafter completion of reaction, product
  6. extractionwas extracted with 120 lit. methylene chloride
  7. customLayers were separated
  8. washorganic layer was washed with 72 lit. brine solution
  9. dry with materialdried (magnesium sulfate)
  10. concentrationconcentrated under reduced pressure
  11. customThe residual mass obtained
  12. stirringstirred for 17 hr
  13. customat 78° C

Sources & evidence

ORD record
ord-f1017fd9395349e8826a492e3602dec4
Source dataset
uspto-grants-2012_05
Patent number
US08173816B2

Reaction notes

Loading…