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

HRID 716017노트

반응식

HRID 716017 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-9f98bb63360a43ae821ff66a05735101
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187495B2

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