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

HRID 73325

反応式

HRID 73325 の反応式
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

参加物

6

反応物 4

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

生成物 1

HCID 584372413-Benzyloxy-4-methylbenzoic acid benzyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-eb540d2fe06f4c57852af25909ee3035
出典データセット
uspto-grants-2014_09
特許番号
US08829040B2

関連ノート

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