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

HRID 467935
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HRID 467935 반응식
[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]
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

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온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-22f562b031894f158d3d18db16e84b90
출처 데이터셋
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08623896B2

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