Potassium Carbonate → 4-(hydroxymethyl)-2-(trifluoromethyl)benzoic Acid

HRID 467934노트

반응식

HRID 467934 반응식
Br[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(=O)([O-])[O-:17].[K+].[K+]>O>[OH:17][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

참가 물질

4

반응물 2

HCID 11430Potassium CarbonateHCID 595634854-(Bromomethyl)-2-(trifluoromethyl)benzoic acid

생성물 1

HCID 110961264-(hydroxymethyl)-2-(trifluoromethyl)benzoic Acid수율 89.5%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
95 °C

실험 절차

To a suspension of 4-bromomethyl-2-trifluoromethyl-benzoic acid (Example I7) (13.03 g) in water (200 ml) was added potassium carbonate (31.1 g). The reaction mixture was stirred at 95° C. for 1 hour. The reaction mixture was then allowed to cool to ambient temperature and was quenched by addition of aqueous hydrochloric acid (5M) (250 ml). The mixture was extracted with ethyl acetate (3×150 ml). The extracts were dried over sodium sulfate and concentrated. The residue was crystallized from ethyl acetate and heptane to give 4-hydroxymethyl-2-trifluoromethyl-benzoic acid (9.07 g) as a white crystalline powder. 1H-NMR (DMSO-d6, 400 MHz): 13.5 (br s, 1H), 7.81-7.66 (m, 3H), 5.53 (s, 1H), 4.62 (s, 2H).

후처리

  1. temperatureto cool to ambient temperature
  2. customwas quenched by addition of aqueous hydrochloric acid (5M) (250 ml)
  3. extractionThe mixture was extracted with ethyl acetate (3×150 ml)
  4. dry with materialThe extracts were dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was crystallized from ethyl acetate and heptane

출처 및 근거

ORD 기록
ord-0e77d6e2ad4447e6a46dda4d69265b26
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623896B2

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