Methanol → Methyl (3-(trifluoromethyl)phenyl)acetate

HRID 5603

反応式

HRID 5603 の反応式
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([CH2:9][C:10]([OH:12])=[O:11])[CH:6]=[CH:7][CH:8]=1.[CH3:15]O>CCOC(C)=O>[CH3:15][O:11][C:10](=[O:12])[CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:13])([F:14])[F:1])[CH:4]=1

参加物

4

反応物 2

HCID 887MethanolHCID 676953-(Trifluoromethyl)benzeneacetic acid

生成物 1

HCID 2734603Methyl (3-(trifluoromethyl)phenyl)acetate収率 89%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

Into a solution of 3-trifluoromethylphenylacetic acid (20.0 g. 98 mmol) in MeOH (100 mL), cooled in an ice-water bath, was bubbled HCl (g) for 15 min. The mixture was allowed to warm to room temperature and was then concentrated in vacuo to furnish a clear, yellow-green liquid which was diluted with EtOAc (0.25L) and washed with saturated aqueous NaHCO3 (2×0.25L), brine (0.25L), and dried (Na2SO4). Concentration in vacuo provided the crude ester which was purified by chromatography on a column of silica gel(230-400 mesh, 600 g, 70 mm o.d., ethyl acetate-hexanes 10:90, 400 mL fractions) using the flash technique. Fractions 6-9 provided 19.08 g (89%) of methyl-3-trifluoromethylphenylacetate as a clear colorless liquid.

後処理

  1. customwas bubbled HCl (g) for 15 min
  2. concentrationwas then concentrated in vacuo
  3. customto furnish a clear, yellow-green liquid which
  4. washwashed with saturated aqueous NaHCO3 (2×0.25L), brine (0.25L)
  5. dry with materialdried (Na2SO4)
  6. concentrationConcentration in vacuo
  7. customprovided the crude ester which
  8. customwas purified by chromatography on a column of silica gel(230-400 mesh, 600 g, 70 mm o.d., ethyl acetate-hexanes 10:90, 400 mL fractions)

出典と根拠

ORDレコード
ord-1e607e457e3c44ccb98525fa715b1116
出典データセット
uspto-grants-1993_09
特許番号
US05245046

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