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

HRID 619160

反応式

HRID 619160 の反応式
[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

参加物

5

反応物 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium Carbonate2 回HCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)2 回

生成物 1

HCID 37199024-(2-Morpholinoethoxy)benzaldehyde収率 82.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c9ba254f97be4014844008c2051d0a6b
出典データセット
uspto-grants-1999_09
特許番号
US05958929

関連ノート

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