4-Hydroxybenzaldehyde → 4-(2-Morpholinoethoxy)benzaldehyde

HRID 619160

반응식

HRID 619160 반응식
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl.Cl[CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>C(#N)C>[N:20]1([CH2:19][CH2:18][O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1

참가 물질

5

반응물 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium Carbonate2회HCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)2회

생성물 1

HCID 37199024-(2-Morpholinoethoxy)benzaldehyde수율 82.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 4-hydroxybenzaldehyde (4.04 g, 33.08 mmol), in acetonitrile (50 ml) was added K2CO3 (10.1 g), followed by N-(2-chloroethyl)morpholine hydrochloride (6.16 g). The reaction mixture was heated to reflux overnight, additional N-(2-chloroethyl)morpholine hydrochloride (0.6 g) and K2CO3 (0.5 g) were added and the mixture was refluxed for another 3 hours. The reaction mixture was cooled to room temperature, filtered, and the filtrate was treated with DARCO®, filtered and the solvent was stripped. The residue was partitioned between saturated NaHCO3 (150 ml) and ethyl acetate (300 ml). The layers were separated and the organic layer was washed with 1N NaOH, dried over MgSO4, filtered and stripped to afford, as an amber oil, 6.41 g of 4-[2-(4-morpholinyl)ethoxy]benzaldehyde.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. temperaturethe mixture was refluxed for another 3 hours
  4. filtrationfiltered
  5. additionthe filtrate was treated with DARCO®
  6. filtrationfiltered
  7. customThe residue was partitioned between saturated NaHCO3 (150 ml) and ethyl acetate (300 ml)
  8. customThe layers were separated
  9. washthe organic layer was washed with 1N NaOH
  10. dry with materialdried over MgSO4
  11. filtrationfiltered

출처 및 근거

ORD 기록
ord-c9ba254f97be4014844008c2051d0a6b
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05958929

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