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

HRID 377116

반응식

HRID 377116 반응식
[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]

참가 물질

8

반응물 4

HCID 1264-HydroxybenzaldehydeHCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium Hydroxide2회HCID 788945-Ethyl-2-pyridineethanol

생성물 1

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

시약·촉매·용매 3

HCID 159952Benzyltributylammonium chloride촉매HCID 111,2-Dichloroethane용매HCID 962Water용매

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온도
22 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-828def491caf4792a7e5dca6256d166e
출처 데이터셋
uspto-grants-2000_02
특허 번호
USRE036575

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