4-Hydroxybenzaldehyde → p-(2-(Dimethylamino)ethoxy)benzaldehyde

HRID 131269

反応式

HRID 131269 の反応式
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Cl.[CH3:11][N:12]([CH3:16])[CH2:13][CH2:14]Cl.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[CH3:11][N:12]([CH3:16])[CH2:13][CH2:14][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 1264-HydroxybenzaldehydeHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

生成物 1

HCID 84823p-(2-(Dimethylamino)ethoxy)benzaldehyde収率 66.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4-hydroxybenzaldehyde (610 mg) in N,N-dimethylformamide (20 mL) is added successively 2-dimethylaminoethyl chloride hydrochloride (1.08 g) and potassium carbonate (2.0 g), and the mixture is stirred at room temperature for 18 hours. To the reaction mixture is added ethyl acetate, and the mixture is washed with water and saturated brine and dried over anhydrous sodium sulfate. The resultant crude product is purified by column chromatography in silica gel (Solvent; chloroform:methanol=20:1→10:1) to give 4-[2-(dimethylamino)-ethoxy]benzaldehyde (640 mg, yield; 66%) as a pale yellow oil. MS (APCI) m/z: 194 [M+H]+

後処理

  1. washthe mixture is washed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe resultant crude product is purified by column chromatography in silica gel (Solvent; chloroform:methanol=20:1→10:1)

出典と根拠

ORDレコード
ord-9b8e0dd81b794860b5609ed7b69b1ab2
出典データセット
uspto-grants-2008_06
特許番号
US07384952B2

関連ノート

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