Ethylene Glycol → 2-(2,3,4-Trifluorophenyl)-1,3-dioxolane

HRID 716017ノート

反応式

HRID 716017 の反応式
[CH2:1]([OH:4])[CH2:2][OH:3].[F:5][C:6]1[C:13]([F:14])=[C:12]([F:15])[CH:11]=[CH:10][C:7]=1[CH:8]=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[F:5][C:6]1[C:13]([F:14])=[C:12]([F:15])[CH:11]=[CH:10][C:7]=1[CH:8]1[O:4][CH2:1][CH2:2][O:3]1

参加物

6

反応物 4

HCID 174Ethylene GlycolHCID 962WaterHCID 5192262,3,4-TrifluorobenzaldehydeHCID 521998p-Toluenesulfonic acid monohydrate

生成物 1

HCID 867272312-(2,3,4-Trifluorophenyl)-1,3-dioxolane

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Ethylene glycol (348.7 g, 5.62 mol) was added in one portion to a stirred mixture of 2,3,4-trifluorobenzaldehyde (300.0 g, 1.87 mol) and p-toluenesulfonic acid monohydrate (35.6 g, 0.18 mol) in toluene (4.5 L) at ambient temperature. The resulting mixture was heated at reflux with azeotropic removal of water using a Dean-Stark apparatus. The water was removed from time to time (3 hour intervals). After 24 hours, the toluene was removed and the residue was diluted with ethyl acetate (1.5 L) and washed with saturated aqueous NaHCO3 (2×750 mL), water (2×500 mL) and brine solution (500 mL). The organic layers were dried over sodium sulphate and the solvent was removed under vacuum. The crude product was subjected to distillation at 60-70° C. in high vacuum (0.1 mm of Hg) to remove the starting material and impurities. The fraction obtained at 75-85° C. (0.1 mm of Hg) is consistent the title compound. Yield: 300.0 g (78%). 1H NMR (400 MHz, DMSO-d6) δ: 3.9-4.1 (m, 4H), 6.0 (s, 1H), 7.3-7.4 (m, 2H).

後処理

  1. temperatureThe resulting mixture was heated
  2. customThe water was removed from time to time (3 hour intervals)
  3. customthe toluene was removed
  4. additionthe residue was diluted with ethyl acetate (1.5 L)
  5. washwashed with saturated aqueous NaHCO3 (2×750 mL), water (2×500 mL) and brine solution (500 mL)
  6. dry with materialThe organic layers were dried over sodium sulphate
  7. customthe solvent was removed under vacuum
  8. distillationThe crude product was subjected to distillation at 60-70° C. in high vacuum (0.1 mm of Hg)
  9. customto remove the starting material and impurities
  10. customThe fraction obtained at 75-85° C. (0.1 mm of Hg)

出典と根拠

ORDレコード
ord-9f98bb63360a43ae821ff66a05735101
出典データセット
uspto-grants-2015_11
特許番号
US09187495B2

反応ノート

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