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

HRID 377116Notes

Reaction equation

HRID 377116 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][OH:11])=[N:7][CH:8]=1)[CH3:2].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[OH-].[Na+].O[C:26]1[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[CH:28][CH:27]=1>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.O.ClCCCl>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][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

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]-

Reagents, catalysts & solvents 3

HCID 159952Benzyltributylammonium chlorideCatalystHCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Conditions

Temperature
22 °C

Procedure

To a mixed solution of 5-ethyl-2-pyridine ethanol (6.0 kg), benzyltributylammonium chloride (6.2 kg of 50% aqueous solution), 1,2-dichloroethane (30 l) and p-toluenesulfonylchloride (9.2 kg) was added dropwise 8N aqueous solution (10 l) of sodium hydroxide at 25° C. After the solution was stirred at 22±3° C. for 4 hours, p-hydroxybenzaldehyde (5.9 kg) and 3N solution (16 l) of sodium hydroxide, were added, and the mixed solution was stirred at 57±3° C. for 15 hours. After the solution was cooled, water (70 l) was added. The aqueous layer was separated and subjected to extraction with 1,2-dichloroethane (20 l). The organic layers were combined and the combined layer was washed three times with 0.1N aqueous solution of sodium hydroxide and three times with water (30 l). The organic layer was concentrated at not higher than 45° C. under a reduced pressure, whereby 4-[2-(5-ethyl-2-pyridyl)ethoxy]benzaldehyde was obtained as an oil. Quantitative analysis by HPLC (high performance liquid chromatography) showed that 5.98 kg (59.0%) of 4-[2-(5-ethyl-2-pyridyl)ethoxy]benzaldehyde was included in this crude product.

Workup

  1. stirringthe mixed solution was stirred at 57±3° C. for 15 hours
  2. temperatureAfter the solution was cooled
  3. customThe aqueous layer was separated
  4. extractionsubjected to extraction with 1,2-dichloroethane (20 l)
  5. washthe combined layer was washed three times with 0.1N aqueous solution of sodium hydroxide and three times with water (30 l)
  6. concentrationThe organic layer was concentrated at not higher than 45° C. under a reduced pressure

Sources & evidence

ORD record
ord-828def491caf4792a7e5dca6256d166e
Source dataset
uspto-grants-2000_02
Patent number
USRE036575

Reaction notes

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