Carbon Dioxide → 4-(Benzyloxy)-2-ethylbenzoic acid

HRID 2220609노트

반응식

HRID 2220609 반응식
C([Li])CCC.[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17](Br)=[C:16]([CH2:21][CH3:22])[CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:23](=[O:25])=[O:24].O>CCCCCC.O1CCCC1.C1(C)C=CC=CC=1>[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([C:23]([OH:25])=[O:24])=[C:16]([CH2:21][CH3:22])[CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

참가 물질

8

반응물 4

HCID 280Carbon DioxideHCID 962WaterHCID 151434711-Bromo-2-ethyl-4-[(phenylmethyl)oxy]benzeneHCID 178418339Butyllithium

생성물 1

HCID 231341484-(Benzyloxy)-2-ethylbenzoic acid수율 51.1%

시약·촉매·용매 3

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매3회HCID 8058Hexane용매

실험 절차

A 1.59 mol/L solution of n-butyllithium in n-hexane (2.28 mL) was added to a solution of 4-benzyloxy-1-bromo-2-ethylbenzene (0.96 g) in tetrahydrofuran (5.35 mL) at −78° C. with stirring. The mixture was stirred for 1.5 hrs at that temperature, poured to dry ice (33 g) slowly, and then tetrahydrofuran (2 mL) was added. The mixture was stirred at room temperature for 40 minutes, and water, toluene and tetrahydrofuran were added. The organic layer was separated, and extracted with a 1 mol/L aqueous solution of sodium hydroxide. These aqueous layers were combined, and was adjusted to pH 3 with an addition of concentrated hydrochloric acid. The aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to afford the title compound (0.432 g).

후처리

  1. stirringThe mixture was stirred for 1.5 hrs at that temperature
  2. stirringThe mixture was stirred at room temperature for 40 minutes
  3. customThe organic layer was separated
  4. extractionextracted with a 1 mol/L aqueous solution of sodium hydroxide
  5. additionwas adjusted to pH 3 with an addition of concentrated hydrochloric acid
  6. extractionThe aqueous layer was extracted with ethyl acetate
  7. washThe organic layer was washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-8bb8ec007c01466d9a46b0552ab0358a
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07417169B2

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