Citric Acid → (3-Isopropoxyphenyl)methanol

HRID 384116

반응식

HRID 384116 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7]C)=O.[H-].[Na+].[C:14](O)(=O)[CH2:15][C:16](CC(O)=O)(C(O)=O)O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>CN(C)C=O.BrC(C)C.O1CCCC1>[CH:15]([O:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:7])[CH:9]=[CH:10][CH:11]=1)([CH3:16])[CH3:14]

참가 물질

9

반응물 5

HCID 311Citric AcidHCID 24758Sodium hydrideHCID 62649Sodium sulfate decahydrateHCID 88068Methyl 3-HydroxybenzoateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 2759474(3-Isopropoxyphenyl)methanol

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 63582-Bromopropane용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of methyl 3-hydroxybenzoate (500 mg) in dimethylformamide (5 ml), 0.463 ml of 2-bromopropane and 197 mg of sodium hydride were added under ice-cooling, and the reaction solution was stirred at room temperature for 5 hours. To the reaction solution was added 10% aqueous citric acid, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to afford a crude product as a yellow oil. To a solution of lithium aluminum hydride (250 mg) in tetrahydrofuran (3 ml), a solution of the crude product in tetrahydrofuran (2 ml) was added under ice-cooling, and the reaction solution was stirred at room temperature for 1 hour. To the reaction solution was added sodium sulfate decahydrate, and the mixture was stirred at the same temperature for 1 hour. The reaction solution was Celite-filtered, and the filtrate was distilled off under reduced pressure. The residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-30:70)) to afford the title compound as a colorless oil.

후처리

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic layers were washed with a saturated saline solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customto afford a crude product as a yellow oil
  7. temperaturecooling
  8. stirringthe reaction solution was stirred at room temperature for 1 hour
  9. stirringthe mixture was stirred at the same temperature for 1 hour
  10. filtrationThe reaction solution was Celite-filtered
  11. distillationthe filtrate was distilled off under reduced pressure
  12. customThe residue obtained
  13. customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-30:70))

출처 및 근거

ORD 기록
ord-004f132c15034215b0b60007b03abc4e
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367708B2

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