Sulfuric Acid → 6-Methoxy-3-(trichloromethyl)-2-benzofuran-1(3H)-one

HRID 2170124노트

반응식

HRID 2170124 반응식
[Cl-].[Cl-].[Ca+2].[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=[O:10].[Cl:15][C:16]([Cl:21])([Cl:20])[CH:17](O)O.OS(O)(=O)=O>>[CH3:4][O:5][C:6]1[CH:7]=[C:8]2[C:12]([CH:17]([C:16]([Cl:21])([Cl:20])[Cl:15])[O:10][C:9]2=[O:11])=[CH:13][CH:14]=1

참가 물질

5

반응물 4

HCID 1118Sulfuric AcidHCID 2707Chloral HydrateHCID 114613-Methoxybenzoic AcidHCID 5284359Calcium Chloride

생성물 1

HCID 1578786-Methoxy-3-(trichloromethyl)-2-benzofuran-1(3H)-one수율 63%

실험 절차

A oven-dried 25 mL three neck round-bottomed flask containing a stirring bar was fitted with a drying tube (CaCl2) and was charged with m-methoxybenzoic acid (5.04 g, 17.91 mmol) followed by chloral hydrate (2.96 g, 17.91 mmol). Concentrated H2SO4 (12.0 mL) was added and the reaction mixture was left stirring at room temperature for 24 h. It was then poured onto ice, a thick precipitate formed and the mixture was left stirring vigorously until the ice was dissolved. The precipitate was filtered, washed with water and dried. The solid was recrystallised from ethanol, the crystals were then filtered and dried to yield 6-methoxy-3-(trichloromethyl)isobenzofuran-1(3H)-one as off-white needles (3.16 g, 63%). Spectral data for this compound were consistent with those in the literature. M.p. 134-136° C. (lit. m.p. 136-137° C.); 1H NMR (400 MHz, DMSO-d6): δ=7.88 (d, J=8.3 Hz, 1H), 7.49-7.39 (m, 2H), 6.54 (s, 1H), 3.90 (s, 3H).

후처리

  1. waitthe reaction mixture was left
  2. additionIt was then poured onto ice
  3. customa thick precipitate formed
  4. waitthe mixture was left
  5. dissolutionwas dissolved
  6. filtrationThe precipitate was filtered
  7. washwashed with water
  8. customdried
  9. customThe solid was recrystallised from ethanol
  10. filtrationthe crystals were then filtered
  11. customdried

출처 및 근거

ORD 기록
ord-53c37fe24b6a4849b58cc420e9a8bac6
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09050586B2

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