Hexamethylenetetramine → 4-Hydroxy-3-(trifluoromethyl)benzaldehyde

HRID 749680노트

반응식

HRID 749680 반응식
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:24](O)=[O:25]>>[OH:9][C:4]1[CH:5]=[CH:6][C:7]([CH:24]=[O:25])=[CH:8][C:3]=1[C:2]([F:10])([F:11])[F:1]

참가 물질

4

반응물 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 679582-Trifluoromethylphenol

생성물 1

HCID 70215934-Hydroxy-3-(trifluoromethyl)benzaldehyde수율 36%

실험 절차

A solution of 2-trifluoromethyl phenol (5.0 g, 30.86 mmol) and hexamethylenetetramine (8.64 g, 61.72 mmol) in trifluoracetic acid (50 mL) was heated at 65° C. for 18 h. At the end of this time the solution was concentrated and diluted with a 2N aqueious solution of hydrochloric acid. The acid phase was extracted twice with ethyl acetate and the combined organic extract dried over magnesium sulfate and concentrated. The residue was subjected to chromatography via Biotage (FLASH 40 M, silica, 20% ethyl acetate/hexane) to yield 2.1 g (36%) of 4-hydroxy-3-(trifluoromethyl)benzaldehyde. MS (ES) m/z 188.9; HRMS: calcd for C8H5F302, 190.0242; found (ESI, [M+H]+), 191.0324.

후처리

  1. concentrationAt the end of this time the solution was concentrated
  2. additiondiluted with a 2N aqueious solution of hydrochloric acid
  3. extractionThe acid phase was extracted twice with ethyl acetate
  4. extractionthe combined organic extract
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-10f1248433134a88b465a81a6d83edc7
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07402698B2

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