Methanol → Methyl 2-(4-methylphenoxy)benzoate

HRID 466428노트

반응식

HRID 466428 반응식
[CH3:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:23]O>>[CH3:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9]([O:11][CH3:23])=[O:10])=[CH:4][CH:3]=1

참가 물질

4

반응물 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 5786562-(4-Methylphenoxy)benzoic acid

생성물 1

HCID 618012Methyl 2-(4-methylphenoxy)benzoate

실험 절차

A solution of 37.70 g of 2-(4-methylphenoxy)benzoic acid was 12.0 mL of concentrated sulfuric acid in 500 mL of methanol was refluxed for 14 hours. After cooling, the reaction mixture was concentrated in vacuo and the residue was added to a mixture of methylene chloride and water. The organic phase was separated, washed with saturated sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was kugelrohr distilled (120°-135°/0.025 torr) to furnish 35.08 g of methyl 2-(4-methylphenoxyl)benzoate, m.p. 31°-34°. NMR (200 MHz, CDCl3) δ 7.87 (d of d, 1H); 7.39 (t of d, 1H); 7.11 (m, 3H); 6.88 (m, 3H); 3.81 (s, 3H); 2.30 (s, 3H).

후처리

  1. temperaturewas refluxed for 14 hours
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. additionthe residue was added to a mixture of methylene chloride and water
  5. customThe organic phase was separated
  6. washwashed with saturated sodium bicarbonate solution and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. distillationThe crude product was kugelrohr distilled (120°-135°/0.025 torr)

출처 및 근거

ORD 기록
ord-b0d9677facc544c1a4fb5b3cfe2bdb6b
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05155118

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