4-Hydroxybenzaldehyde → 4-[(11-Hydroxyundecyl)oxy]benzaldehyde

HRID 2204905ノート

反応式

HRID 2204905 の反応式
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[OH:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][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 4875Potassium IodideHCID 11430Potassium CarbonateHCID 7416311-Bromo-1-undecanol

生成物 1

HCID 149659774-[(11-Hydroxyundecyl)oxy]benzaldehyde収率 58%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

50.0 g (409 mmol) of 4-hydroxybenzaldehyde and 123.0 g (490 mmol) of 11-bromoundecan-1-ol are dissolved in 400 mL of N,N-dimethylformamide. 113.0 g (819 mmol) of potassium carbonate and 7.0 g (42 mmol) of potassium iodide are added and the suspension is heated to 80° C. After 48 h, the excess of potassium carbonate is filtered off and the resulting filtrate is poured to icy water. The aqueous layer is extracted twice with ethyl acetate. Combined organic layers are washed with brine, concentrated to minimum volume and precipitated in cold heptane. The precipitate is filtered off and washed with cold heptanes. 69.4 g of 4-[(11-hydroxyundecyl)oxy]benzaldehyde are obtained as a white solid (57% yield). This material proves chromatographically homogenous and displays spectral characteristics consistent with its assigned structure.

後処理

  1. filtrationthe excess of potassium carbonate is filtered off
  2. additionthe resulting filtrate is poured to icy water
  3. extractionThe aqueous layer is extracted twice with ethyl acetate
  4. washCombined organic layers are washed with brine
  5. concentrationconcentrated to minimum volume
  6. customprecipitated in cold heptane
  7. filtrationThe precipitate is filtered off
  8. washwashed with cold heptanes

出典と根拠

ORDレコード
ord-70358ccca6174fb893e0bb20dcb1f167
出典データセット
uspto-grants-2016_06
特許番号
US09366906B2

反応ノート

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