Benzyl Bromide → 3-Benzyloxy-4-methylbenzoic acid benzyl ester

HRID 73325

반응식

HRID 73325 반응식
O[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1C)[C:5](O)=O.[C:12](=[O:15])([O-])[O-:13].[Cs+].[Cs+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:26](=[O:29])(O)[O-].[Na+]>CN(C)C=O>[CH2:18]([O:13][C:12](=[O:15])[C:10]1[CH:2]=[CH:3][C:4]([CH3:5])=[C:8]([O:29][CH2:26][C:2]2[CH:3]=[CH:4][CH:8]=[CH:9][CH:10]=2)[CH:9]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

6

반응물 4

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 685123-Hydroxy-4-methylbenzoic acidHCID 516892Sodium Bicarbonate

생성물 1

HCID 584372413-Benzyloxy-4-methylbenzoic acid benzyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-hydroxy-4-methylbenzoic acid (5.0 g) in N,N-dimethylformamide (100 mL) were added cesium carbonate (32 g) and benzyl bromide (12 g) at the same temperature and this mixture was stirred at room temperature for 2 days. To this reaction mixture was added a saturated aqueous sodium bicarbonate solution and this mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and this residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate) to give the title compound (7.5 g).

후처리

  1. extractionthis mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthis residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-eb540d2fe06f4c57852af25909ee3035
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829040B2

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