Benzoyl chloride → 2-Benzoyl-5-methoxybenzoic acid

HRID 29918

반응식

HRID 29918 반응식
Br[C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C([Li])CCC.CCCCCC.[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1COCC1.O>[C:24]([C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

참가 물질

7

반응물 4

HCID 7412Benzoyl chlorideHCID 8058HexaneHCID 899062-Bromo-5-methoxybenzoic acidHCID 178418339Butyllithium

생성물 1

HCID 3340802-Benzoyl-5-methoxybenzoic acid

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

A solution of 2-bromo-5-methoxybenzoic acid (5 g, 21.6 mmol) in 50 mL of THF is stirred under argon at −78° C., and a 1.6 M solution of n-butyllithium in hexane (29 mL, 45 mmol) is then added dropwise. The reaction mixture is stirred for 1 hour at −78° C. and benzoyl chloride (3.2 g, 22.7 mmol) is then added dropwise. The reaction mixture is stirred for 1 hour 30 minutes at −78° C. and then for 18 hours at room temperature. The mixture is hydrolysed with 100 mL water and then washed with ethyl acetate. The aqueous phase is acidified by addition of 5 N hydrochloric acid and then extracted with ethyl acetate. The organic phase obtained is washed with brine and then dried over anhydrous sodium sulfate. After filtration and evaporation under reduced pressure, 5.4 g of a colourless oil are obtained, and are used without purification.

후처리

  1. stirringThe reaction mixture is stirred for 1 hour 30 minutes at −78° C.
  2. waitfor 18 hours at room temperature
  3. washwashed with ethyl acetate
  4. additionThe aqueous phase is acidified by addition of 5 N hydrochloric acid
  5. extractionextracted with ethyl acetate
  6. customThe organic phase obtained
  7. washis washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationAfter filtration and evaporation under reduced pressure, 5.4 g of a colourless oil
  10. customare obtained
  11. customare used without purification

출처 및 근거

ORD 기록
ord-925758cac70f47c8b4ab12e182b17ff3
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423030B2

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