3-Hydroxybenzaldehyde → HCID 21071449、化合物

HRID 1666881ノート

反応式

HRID 1666881 の反応式
[F:1][C:2]([F:19])([CH:16]([F:18])[F:17])[CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1C)S([O-])(=O)=O.[OH:20][C:21]1C=C(C=CC=1)C=O.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:19][C:2]([F:1])([CH:16]([F:17])[F:18])[CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[CH:21]=[O:20]

参加物

5

反応物 3

HCID 1013-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 21071450HCID 21071450、化合物

生成物 1

HCID 21071449HCID 21071449、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
92 °C

実験手順

Combine 3-(2,2,3,3-tetrafluoropropoxy)tosylate (200 g, 0.664 mol), 3-hydroxybenzaldehyde (101.7 g, 0.833 mol), dimethylformamide (1.5 L) and powdered potassium carbonate (192 g). Heat under stirring at 92° C. for about 22 h. Cool the reaction mixture to 40° C., pour over ice-water and extract with ethyl acetate. Combine organic phases, wash with 1 N sodium hydroxide (1 L and 0.5 L) and then a solution of saturated sodium hydrogen carbonate, dry over magnesium sulfate, filter, evaporate to dryness to provide a oily residue. Distill the oily residue under reduced pressure in a Claisen flask to give a first fraction of the title compound: bp 108-110° C. under 0.4-0.5 mmHg and a second fraction at 110-111° C. under 0.4-0.5 mmHg.

後処理

  1. temperatureHeat
  2. temperatureCool the reaction mixture to 40° C.
  3. extractionextract with ethyl acetate
  4. washCombine organic phases, wash with 1 N sodium hydroxide (1 L and 0.5 L)
  5. dry with materiala solution of saturated sodium hydrogen carbonate, dry over magnesium sulfate
  6. filtrationfilter
  7. customevaporate to dryness
  8. customto provide a oily residue
  9. distillationDistill the oily residue under reduced pressure in a Claisen flask

出典と根拠

ORDレコード
ord-6ee8a3e00db442b5a4dbd1fa041c873a
出典データセット
uspto-grants-2011_10
特許番号
US08044090B2

反応ノート

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