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Sulfuric Acid → Methyl 4-(hydroxymethyl)-2-(trifluoromethyl)benzoate

HRID 467935
ノート
印刷プレビュー

反応式

HRID 467935 の反応式
[OH:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([C:12]([F:15])([F:14])[F:13])[CH:4]=1.[C:16]1(C)C=CC=CC=1.S(=O)(=O)(O)O>CO>[CH3:16][O:8][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:3]([CH2:2][OH:1])=[CH:4][C:5]=1[C:12]([F:13])([F:14])[F:15]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 1140TolueneHCID 110961264-(hydroxymethyl)-2-(trifluoromethyl)benzoic Acid

生成物 1

HCID 57443316Methyl 4-(hydroxymethyl)-2-(trifluoromethyl)benzoate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
80 °C

実験手順

To a solution of 4-hydroxymethyl-2-trifluoromethyl-benzoic acid (Example I8) (9.07 g) in methanol (250 ml) was added toluene (250 ml) and concentrated sulfuric acid (4.5 ml). The reaction mixture was stirred at 80° C. for 16 hours. The methanol was removed and the residue diluted with aqueous sodium hydrogen carbonate (saturated) (150 ml) and ethyl acetate (150 ml). The phases were separated and the aqueous layer was extracted with more ethyl acetate (2×150 ml). The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated to give 4-hydroxymethyl-2-trifluoromethyl-benzoic acid methyl ester (5.97 g) as a colorless oil. 1H-NMR (CDCl3, 400 MHz): 8.76-7.27 (m, 3H), 4.78 (s, 2H), 3.93 (s, 3H), 2.5 (br s, 1H).

後処理

  1. customThe methanol was removed
  2. additionthe residue diluted with aqueous sodium hydrogen carbonate (saturated) (150 ml) and ethyl acetate (150 ml)
  3. customThe phases were separated
  4. extractionthe aqueous layer was extracted with more ethyl acetate (2×150 ml)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-22f562b031894f158d3d18db16e84b90
出典データセット
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08623896B2

反応ノート

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