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

HRID 882102Notes

Reaction equation

HRID 882102 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>C1(C)C=CC=CC=1.O.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 83%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 6386tert-ButanolSolvent

Procedure

Into a stirred mixture of 4.5 lit. tert-butanol and 13.5 lit. water was added 1.2 Kg (9.02 mole) 5-ethyl-2-vinyl-pyridine at 25° C. To this was added 1.926 Kg (10.82 mol) N-bromosuccinimide and reaction mixture was stirred for 1.5 hr. 13.5 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 12 lit. methyl tert-butyl ether. Layers were separated, organic layer was washed with 7.2 lit. brine solution, dried (magnesium sulfate) and concentrated under reduced pressure. The residual solid obtained was added into a stirred mixture of 1.59 Kg (13 mol) 4-hydroxy benzaldehyde dissolved in 13 lit. toluene and 523 g (130 mol) NaOH dissolved in 120 lit. water. To this was added 221 g PEG 2000 and stirred for 17 hr. at 78° C. Subsequent work-up gave 2.029 Kg (83%) 4-[2-(5-ethyl-pyridin-2-yl)-2-hydroxy-ethoxy]-benzaldehyde, m.p. 81° C.

Workup

  1. additionTo this was added
  2. stirringstirring
  3. waitwas continued for further 45 min
  4. customProgress of reaction
  5. customafter completion of reaction, product
  6. extractionwas extracted with 12 lit. methyl tert-butyl ether
  7. customLayers were separated
  8. washorganic layer was washed with 7.2 lit. brine solution
  9. dry with materialdried (magnesium sulfate)
  10. concentrationconcentrated under reduced pressure
  11. customThe residual solid obtained
  12. stirringstirred for 17 hr
  13. customat 78° C

Sources & evidence

ORD record
ord-e7f46dcd6a964d6dac3c3a80ca268573
Source dataset
uspto-grants-2015_03
Patent number
US08993773B2

Reaction notes

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