4-Hydroxybenzaldehyde → Benzaldehyde, 4-[2-(5-ethyl-2-pyridinyl)ethoxy]-

HRID 377115

Reaction equation

HRID 377115 reaction equation
[OH-].[Na+].[CH2:3]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][OH:13])=[N:9][CH:10]=1)[CH3:4].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.O[C:26]1[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[CH:28][CH:27]=1>O.[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.C(Cl)Cl>[CH2:3]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][O:13][C:26]2[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[CH:28][CH:27]=2)=[N:9][CH:10]=1)[CH3:4]

Participants

8

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium Hydroxide2×HCID 788945-Ethyl-2-pyridineethanol

Product 1

HCID 9881522Benzaldehyde, 4-[2-(5-ethyl-2-pyridinyl)ethoxy]-Yield 114%

Reagents, catalysts & solvents 3

HCID 159952Benzyltributylammonium chlorideCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of sodium hydroxide (5 g) in water (30 ml), were added methylene chloride (100 ml), 5-ethyl-2-pyridineethanol (15 g) and benzyltributylammonium chloride (50% aqueous solution, 6 g), p-toluenesulfonyl chloride (23 g), and the mixture was stirred at room temperature for 2 hours. To the reaction mixture were added p-hydroxybenzaldehyde (12 g), water (100 ml) and sodium hydroxide (8 g) and the mixture was stirred at 40°-50° C. for 12 hours. The reaction mixture was separated into two phases and the methylene chloride layer was dried (MgSO4) and concentrated to give 28.6 g of crude 4-[2-(5-ethyl-2-pyridyl)ethoxy]benzaldehyde as oil. This oil was purified by silica gel chromatography to give 15.8 g (62%) of pure 4-[2-(5-ethyl-2-pyridyl)ethoxy]benzaldehyde as oil.

Workup

  1. stirringthe mixture was stirred at 40°-50° C. for 12 hours
  2. customThe reaction mixture was separated into two phases
  3. dry with materialthe methylene chloride layer was dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-987d641a6d834cd5a8e3840d83e906e8
Source dataset
uspto-grants-2000_02
Patent number
USRE036575

Linked notes

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